Our Collabsphere Session about O365 from the viewpoint of an Admin and a User

Hogne Pettersen and I gave this session today at Collabpshere.

It is a mix of good, bad, bewildering, and impressive views about the whole O365 story, solution, and parts within it.

We could spend all day discussing this and are happy to do so if anyone wishes to ask for our help.

For more details, follow us on our Twitter accounts at @LotusEvangelist and @NordicCUG

Shoot me NOW! The Life and Death of an O365 Admin and User from Keith Brooks

Peek a Boo with O365 and Bits

Collaboration means different things to different people. Business collaboration is about sharing of
information, ideas, details, actions, and presuming everyone does the same in return so you truly reach that 1+1=3 world.

I am spending sometime on a side project with a company that is leveraging O365. On the outside looking in, it seems to be just what one wants for work. Online shared space for files, email, IM, ESN(Enterprise Social Network), team/group space, Office tools, and much more all wrapped up in one price and available only in the Cloud.

The first thing I experienced, and keep in mind I am accustomed to being the admin usually, was my name was spelled incorrectly. In general, not the end of the world, however, in some cases, my logins were correct, but it appears not in AD. When I asked IT to correct it, they told me it would take most of a day to do this because they would now have to go change all the other systems that I have logins for and fix them as well. SSO is not available in O365? And to rename an ID takes hours? As an admin, I am bemused at the discussions.

Normal users probably just shrug it off as IT time and plans.

My login aside, the quirks of O365, as some of my friends call them, are more a skewed view based on other products and our own expectations.

It seems one can not change the colors on screen for Outlook (2010 edition they use here). The choice is limited to 3 colors, none of which are even remotely exciting, Blue, Silver, Black. Cowboys and Raiders colors? What about us Dolphin fans that want orange or green? Or just set to Windows Desktop theme colors? Evidently 2013 is no better about this.

I will post this next bit, as it is important, but want to point out it is not unique to Microsoft. The multiple profiles, pictures, details issue is a major PITA to employees. Why can't the entry in AD cover the basics of the person (name, photo, phone, location, email, etc..) and have that, via LDAP, or AD itself, pushed out to any other system connected to it for user accounts? Instead there is Outlook, SharePoint, Yammer, and whatever the O365 bit itself is called all not sharing ANY details, in the case here, not even my login and password for the domain. Yes, WTF indeed.

Off I went to create profiles, about me docs, upload photos, enter office details because this is posted on the Yammer home page:

When signing up to Yammer can you please add a recognisable photo of yourself, so people can easily identify you in the office. Also add your phone number(s) and where you are located, including which floor you are on.

As it turns out SharePoint is not connected to O365 here, so I understand that...as an IT person. As an employee it would make me wonder why, if I cared enough, which maybe no one does anymore. Thus why adoption of an ESN is not an easy task inside companies and why I try to help it best I can.

Before some friends jump on this, as some have, be careful, IBM in this case does not handle it any better. Sametime vs. Connections profiles/photos vs. Domino data/profile/photos. Same problem, no solution. I understand why, in both companies products this exists. Simply put, if they have no way to know what "solution" you are installing, they have no way to provide the details efficiently. My argument has always been it should reside in the Directory (AD, Domino, whatever) and let everything else pull it from there. Whatever, live with it, do not slam either for this shortcoming.

The login and password thing is more bewildering to me. My Windows Domain login and password do not match my Outlook or Yammer ones but does SharePoint. A hybrid model that works as designed I guess but SSO or SPNEGO or even Oauth, anything/something would be a better solution.

On the plus side, the Yammer mobile client looks good and works well albeit in a multi step process just to message someone. I wait for the "Skype will rule it all" day coming soon, but for now, tick the box, they did mobile. You need to flip back and forth to the option menu to read group messages or the "stream" and to message someone takes 4 steps but it is a simple UI and easy to respond to posts in the stream or groups.

Yammer desktop, in short, does not exist. This is a frustrating thing for someone like myself so used to just sending IMs easily for the last 17+ years from a list in my tray. While one gets notified when there is a message, if you want to send someone a message you have to login (or keep a browser window open) just to then get to your list and try to message the person. I say try because I have not found a way for the web client to sort people by online status or even by alphabetical order. The Skype transition/integration can not come fast enough in my opinion.

Yammer Desktop Notifier is mostly a waste of time since it does NOTHING. To be fair, it has 3 options, (Inbox, Notifications, My feed) that when clicked take you to a browser and the messages. And if something is waiting for you, it has color codes to let you know in the little icon in your tray. But lookup people? Send an IM? No and No. In a corporate desktop world, this is frustrating. In a mobile, non desktop world, this is fine presumably, I have not loaded it yet on my iPad so I have no direct knowledge at this time.

The discussion around dropping SharePoint in favor of Jira is a conversation which I have not gotten into previously but would seem to be a major question/issue for companies that are using SharePoint or any ESN as a project management workflow tool. I may write more on this in a future blog after some further research.

Overall I can't say anything has blown me away that I must have it, aside from Skype. Perhaps Microsoft and other companies providing Enterprise solutions now find themselves in an unusual situation, big ugly/heavy clients that we use 10% of the benefits have passed their sale dates. When you really have better apps on your phone than your office, we are no longer on the "when will we get updates" discussion, but on the "why can't we use this app" or just doing it anyway. This is not a new opinion, we have been discussing it for years, but as I saw first hand, when IT people and executives are no longer willing to adjust to employees needs, then we in IT have failed and it matters little which vendor you chose.

Have You Designed a Car without an Engine Today?

Half baked ideas? No, they were completely baked and ready to go....except for a strategic piece. Lost in translation or just lost in space, hard to know sometimes where to assign the lack of accountability.

A Cloud solution that is not quite ready for the Enterprise or an application that you are working on when you suddenly realize no one thought about who would use the solution, let alone, why they need it.

Governments, countries, airports and many organizations run into this it seems more often today than ever before. The site, Why Projects Fail, might be useful to you.

Imagine if in walks your business leader with an announcement of a cool new car they dreamed up for the company to produce. It's just a drawing right now, maybe a clay model, but they have a vision!. They have searched out some vendors that promise to make everything nice and clean, like never before, and they asked to let them do everything so the leader can focus on the end game. Agreements are made and a date set to expect everything to be ready for the "1st auto show of the year".

Shortly before the eagerly expected date, the leader calls the vendor and asks if everything is ready. They reply, yes, of course, we made sure you have roads from your office to the show. The leader is confused and asks, where is the engine for the car we designed? The vendor replies no one said anything about the engine, we provide the roads for you to drive and look how nice they are all black and smooth topped."Where's my engine!?" screams the leader. Engine? Replies the vendor, we don't do engines.

I have been in numerous meetings over the years where parts of these discussions went on and I wondered why it happened in the first place.

Would better meetings help? Would an ESN like IBM Connections or Microsoft Sharepoint or Jive? Was there a problem in Microsoft Project? Not enough project managers? Too few? If you had used a different email system none of this would have happened.

It is easy to be carried away by the excitement of a new project and just as easily to be led astray. Just because the client asks to go to the Cloud does not mean you should block it, or help, without some clear logic and information.

Last night I wrote and compiled a two page list of questions for a client that wants to migrate mail systems... to Domino. I broke up the questions, some 60 or so, into 3 groups, the "old info" , the "future info" and the "co-existence".

The actual list could be 80 pages, like an SUT document I worked on previously, or one page. The questions and answers will come but being prepared is more important.

Fud Buster Friday #60: Sharepoint is the Future

I love this graphic, no idea if it really was used but thanks to Sharepoint magazine for sharing it.

In a blog post, A Guide to Leaving Lotus Notes and Moving to Microsoft SharePoint, by Andrew Vevers which was a finalist entry for the Aspiring Authors Competition 2011 according to the post, we see a classic case of ignoring the obvious.

What is the focus really about here? Is it to gain Mr. Vevers new clients? Is it to be used as a sales tool to persuade companies to move off Lotus Domino? Maybe to teach other consultants how to make money off their clients? Like this line:

"If you think they might not be sure what they need to keep, consider offering to migrate the last six months’ data or implement a per-GB data migration charging model. That’ll get them thinking!"

No, I believe the focus is entirely misguided. It is focused on the past. Cleaning the data? Design? For what? To "convert" to Sharepoint? Really? Is that the best you can offer your clients Mr. Vevers? The past? Like this line:

"Despite these factors, your main focus should always be on reproducing the functionality, not adding unnecessary bells and whistles."

What about the future? Don't you think that if you were going to convince people to move off a well used platform that it should be to something new, improved and providing more benefits? But the bells and whistles could have been part of the Domino application all along, even in R7 where he last left his Lotus knowledge.

The discussion never hits web apps and stays focused on Notes apps.

While I agree that companies should have been building apps for the web for years, it has not always been their focus until the last 2-3 years, Notes applications are not impossible to update for the web. Recent efforts have been made to transform apps to Xpages and more web/mobile access and perhaps this would be a cheaper solution in some cases, if not all.

Those of you in a similar situation, the crossroads of business and technology should keep in mind. The future is bright but only if you can see it. If you can enhance your applications, do it. Be agile, customer centric, responsive. Help your management see the better future, do a mockup, do something. If you are an employee it costs you and the company nothing more to enhance your apps, and you should be doing it no matter who owns the app or how old it is. Your administrators will get their job done and get you to 8.5.2 but if you aren't helping the apps, then why bother going beyond R5 or R6?

Sharepoint is not the future. It may be new and shiny, but it is NOT the future nor does it represent it in any way, shape or form. It is just another platform which just happens to be licensing, server and hardware heavy. Posts like Mr. Vevers do not fairly discuss the issue because it is presumed already one will be migrating.

I don't believe that many companies have removed Domino from their data centers and I do not believe many will still for years to come. I believe at least 85% of the Fortune 500 still run Domino applications today and I hope at some point IBM will bring back the campaigns that highlighted the usage across industries because it is true and it is important to get that information into the minds of executives.

Sharepoint Symposium 2010 Reviewers: Need Enough Money and Take an Ibuprofen

KMWorld, a periodical I used to read quite often, but have been turned off by it of late because it has become a rag sheet for Sharepoint and Microsoft, showed up in the mailbox the other day.
IBM advertises in there and sometimes there are even articles about IBM software and solutions on the website and in print. But it really is a MS lovefest (see the series titled: SharePoint: The Reality Series 8 Implementing SharePoint 2010—An ECM manager’s view. To be fair, they do point out downsides, but overall what do you think when they created a Sharepoint Symposium anyway?

So on the cover of the January 2011 issue I was surprised to see a review of the Sharepoint Symposium 2010 that produced some interesting points.

You can read the entire article here, below is 2/3 of it. Bold text added by me.

We created the SharePoint Symposium to praise SharePoint, not to bury it. After all, the total number of seats worldwide likely tops 130 million! It’s easy to view it as a veritable panacea, especially for an organization committed to a .Net environment. It is not, however, without its shortcomings.

Nevertheless, you can use the platform for virtually anything—records management, corporate portal, Web content management, collaboration, business process management, digital asset management ... “as long as you have enough money and ibuprofen,” adds Tony Byrne, Symposium co-chair and president of the Real Story Group.

For all its remarkable characteristics, SharePoint is not a collection of best-of-class capabilities. Search is a perfect case in point. Even though it has improved in 2007 and 2010, it might certainly make better sense to license a mid-range search product, many of which are easier to install and administer and might likely be cheaper than the high-performance FAST search. Arguably, the same can be said about each component of the platform....

One thing that holds true for all SharePoint deployments is the imperative of creating a good governance strategy. The ease with which sites can be created, populated and then abandoned has resulted in a near-viral situation. For many organizations, it’s getting out of control, as witnessed by the overflowing audience at the Symposium’s governance session in Washington, D.C., in November.

From a document management perspective, or a collaboration solution perspective, the last paragraph rings true. The "it's in a database" problem of years ago seems to be updated for modern times and not just in Sharepoint.

Nice to know that not everyone, even Microsoft Business Partners, admit there are issues there.

The End Game of Migration

We get a call from a 3rd party, rarely the client, asking us to manage a companies Lotus infrastructure for 3-6 months. Should be the client, we are trying to figure out how to market to the SMB and unknown Lotus customers, thus my post the other day about SEO.

My usual reply is why/when are they going to Exchange/Sharepoint? Prescient I know.

Usually they are small shops that use only mail, but sometimes I recognize the company and KNOW they have applications too. So what's going on?

Sharepoint? .Net? Gmail?

Our job is to smooth the integration between Domino and whatever the client is going to be using in the future. Ideally we never go on site for this, after all if you are leaving this excellent mail system for another one, we are just caretakers now. If we were on site, we would fix your environment, then you would look bad for leaving it.

(There is really no need for us to be on site more than once a week for meetings for reasons I will detail in some other post.)

Integration? "No, we don't want integration, we are dropping Lotus" each client says. Really I inquire. have you thought about....and any number of routes take place after I listen to them explain why they are doing it.

The truth is, unless they really ONLY use it for email(and even in these cases sometimes), Domino is going to be hanging around for a while.

Why is this? A few reasons:

1) Fear - What if Exchange/Sharepoint/Gmail is, OMG, worse! Or the users revolt or a million other ideas that pop into people's heads.

2) Complexity - What's so complex about email? Well Calendar and Scheduling can be troublesome and in some companies the Lotus resource database is the best thing out there for scheduling conference rooms, training etc.

3) Applications - Naturally they say they will rewrite the apps. In 15+ years of this I have heard way more stories of companies spending millions to go to a different platform only to find nothing worked as well or robustly as their Domino apps. Don't believe me and in the middle of it now or thinking about it? Email me, I can connect you with some large companies that do nearly all development on Domino.

4) Time - Sure you could cut over everyone in a weekend, even a day. But you big companies will never do that of course. So the process drags on for a long time, years in fact based on various reports. Small companies can do it quicker, but they fear upheaval so it also take a little bit of time.

5) Time #2 - Here is where the integration kicks in. If you do not cut over everyone at once, you add some expenses to the mix. The Connector between Exchange and Domino must get put in or you have some fidelity issues, of course you can work around it for free using Domino. However, most Microsoft Business Partners will tell you to install(with yet more licenses and CALs and hardware) the connector to integrate the directories between AD and Domino.

6) BES - Blackberry users cause you to also have a 2nd BES in place, one for Domino and one for Exchange. Sure once everyone moves off the old one you can repurpose it, but in the mean time it means more money, hardware, licenses, support.

7) Fax - Lotus Fax Server or some other specific version for Domino would require new hardware, licenses and services/support to now have 2 routes, one for each system.

8) More reasons and some of you out there can add to this in various ways.

So the next time you or your boss or client says they need short term help for the migration, think again and realize a partner that has done it and can manage it for you properly may just make your life easier.

Microsoft Stores Live POC

I see my friend Bilal, of the Lotus Foundations team already posted on this, but let's see it in a different light.

As many know by now, Microsoft plans on having stores, a la Apple.

What they may be thinking is the new hardware they are coming out with will really impress everyone. We should only be so lucky to see those new Microsoft mouse and keyboard designs.(in spirit of truth in writing, I have a wireless Microsoft keyboard/mouse combo and they work fine).

What do they think they can accomplish? Better yet, who will be working there? I would bet not the best and brightest of Redmond. Thus easy pickings for anyone that wants to go convert a bunch of customers to Lotus or any other product.

Just imagine going in there and asking why Exchange or Sharepoint for that matter can't send a 100MB attachment or store it without causing issue. I know someone will say they do it, but I bet the store limits attachments to 10MB or something small.
So go test and have fun.

While you are at it, ask them to show you in a graphical representation the network architecture in the store which will enable them to use Sharepoint with Exchange. Raise your hand if you think it's only 2 servers. Sorry you must be a CIO in Microsoft's pocket if you still think that! Go read my other posts start here and get your head around how much it will cost and how many cals, licenses, servers you will need.
Lotus has you on this one Redmond.

What I think you may see from the stores, potentially, is a POC location. Every store, quite easily, could be rolled out with ALL the products running and in synch and easily shown or detailed live so customers can see it does all work together so well. But remember to count the # of servers, it will be staggering. Even if they use a central one, which we know they can't because Exchange and Sharepoint do not play well across a WAN, it will still be interesting to see.

Also will they ban people like me from their stores fort harassing the "tech" staff?

Sharepoint, The Cloud and the Environment

An article in Information Week, which appeared slightly different in print from the online version covered some pros and cons.

The software's Swiss Army knife approach helps companies create more useful intranets, set up document sharing, offer blogs and wikis, and build a richer online company directory. This boundary-blurring nature is part of its appeal..

J. Nicholas Hoover, the author of the article could be describing Domino but no, it's Sharepoint.

While IT manages master page layouts, business units can build one-off sites without IT's help. "This is why SharePoint has taken off like wildfire

General Mills Manager of .NET

So how do we counter this? What can we do? What should Lotus do?

Sharepoint is already under the covers, maybe even paid for in licensing, so why not use it? Sound familiar? It should, Lotus asks the same question, and has for years.

When you put Domino into your organization, you had, from early on, the capability to do so much more, but few understood it all or do today. The discussion databases that predate wiki's, the Team Room's that predate most collaboration software in the market, plus a built in messaging system and strong server options all provides a great package.

Now it looks like companies want to go modular. Server for this, a server for that.

Doesn't this go against the thinking of modern times?
Less power consumption, fewer servers, reduced carbon footprint, fewer Administrators, reduced expenses?

And now The Cloud hovers ever closer and may provide the myth of all the above.
You as a customer will experience all the benefits just listed, yet your provider/host of Cloud Computing just took it all on.

How are they doing with it? What are they doing to minimize it?

Does this interest you? Will it make any difference for you to go with IBM, Amazon or anyone else?

Defining Lotus Notes & Domino for the Next Gen

In a truly perfect world, The Beatles would never have broken up, Jimi Hendrix would still be alive and MACs would rule the Earth. And Tech shows would get attendees when they are int he right place at the right time.

I went to a tech show today, ITEC, hoping to meet and listen to Chris Brogan. Sadly, as he informed me on twitter, he had to skip us in Ft. Lauderdale.

I ended up meeting a possible new SPAM solution provider for my clients and learned a great deal about using Facebook for Business from Chris's replacement, a really nice guy from Boston, Brett Wohl(He's on Facebook, go say hi!). Thanks Brett!

What I was not prepared for was defining Lotus to him. Sure, I do it all the time, but this was the first time I had really sat and explained it to someone more in tune with Facebook than Redbooks.
I appealed to digital rights and the ability to secure them in the app or db and allowing for selective exposure, plus replication capabilities for working on applications when traveling. We discussed it's messaging side, it's open source side, variable Operating System platforms, and even more important to their customers, scalable clustering within a heterogeneous environment. Even hit on document management and serializing data via RSS and other means.

In a way I feel like I failed to get across what I wanted, but he got what made sense to him and I leveraged what I knew would make sense to him so we were both happy in the end.

We discussed Sharepoint being used as a file sharing program, not in true collaborative style. And that Domino did sharing and does still, long before Sharepoint existed, but then I start to sound like I am 50 or 60!

Another really interesting conversation was with a Microsoft BP, who works in the SMB area. When I asked about his dealings with Lotus customers he said he doesn't see many naturally. He informed me that many customers are still running Windows and Exchange 2000. His hope was for the new Small Business Server, which has Exchange inside, would help migrate these people.

Naturally, Lotus Foundations came to mind and why IBM is pushing that as a solution. I wished him well and continued on.

The Waiting is the hardest part...and most expensive!

You say Lotus is a Legacy solution? Are we that old?

What about Exchange? Well you waited nearly 4 years for an update, was it worth it? You spent 5 years of Software Assurance money with Microsoft and now you wonder how they could afford to buy Yahoo!?!

Outlook also you waited 4 years. IE as well.

You waited 6 years for Vista since XP emerged.

Forgot about Sharepoint, an excellent chart is found here, hopefully IBM SWAT has seen this.
Yep, almost 4 years past.

See a pattern? And on the Lotus side we have seen since 2003 release 6.5 and R7 in 2005 with R8 in 2007 materialize which averages out to a new version every 2 years and in some cases, split stream updates/revisions/addons and enhancements happenned twice a year.

So who is the legacy solution and why do you or your clients think it isn't Microsoft?

Try, Try, Try to Understand

Really, put yourself in someone else's shoes/mind/laptop.
What do you see/hear or know?
Sometimes nothing, you just don't "get" the problem.
It's not unusual, one can't expect to see everything from all angles.
But what if you covered all angles and still don't get it?

So in essence, when someone says they love their Microsoft Sharepoint Server I really do wonder, what do they love? SOme questions I have for you:

Is it the ease which it is installed?
Simplicity of the UI?
It's limitations on the size of files and/or folders(which even Microsoft admits)?
Perhaps the integration to their network?
Could it be the availability to save/move or access the Sharepoint site from their IM client like one can do for Lotus Quickr via Sametime?
Maybe the admins enjoy keeping not one but 2 versions of Sharpeoint running since the 2007 version did not migrate data from the ealrier version?

Does your CFO know you have it and pay for it probably anywhere from 2-4 times, at least, in your Software Assurance and various Microsoft agreements?

It's that last point that may surprise you. I look forward to future discussions about this issue.

LS08 BD DAY: Microsoft's Software Assurance

From what I learned and revisited in Lotusphere today.

I've written a few times about the Exchange side of the equation and even Sharepoint but I learned more today.
And now so will you.

Here's the premise:
Microsoft has offerred you or your client Sharepoint and Exchange for free.
And your client wants the same from IBM to stay with Lotus.

The reason is because they want to put you into an enterprise agreement which has Software Assurance(still an oxymoron). Software Assurance, if you do not know, allows for a company to receive "free" upgrades on their licenses IF new software comes out in the next 3 years or however long you commit to int he agreement.
You can also do this if you know you will be updating soon.
Of course you pay for this benefit...each year of the agreement.
And the cost for SA is about 1/3 of the total licensing cost. So not a small chunk of change.

So let's look at all the companies that bought into it in 2003 for example.
Name one product which you paid for an upgrade that materialized from the "Desktop Professional" or "Professional Desktop" or even the "Enterprise Desktop".

Windows upgrade from XP, nope.... Vista came out in 2007
Office upgrade from Office 2003, nope......office 2007 came out in 2007
Exchange upgrade from Exchange 2003, nope....Exchange 2007
Outlook upgrade from Outlook 2003, nope......Outlook 2007

So what did you pay all that money for in the first place?
Well, MAYBE you were on 2000 and you expected to move to 2003 someday. Fair enough.
What if you bought this in 2004? Same problem. 2005? You start to see a pattern of course.

If your company continues to do this, as one company admin told me today theirs does, not only are you wasting money, you are perpetuating the Microsoft arms in your company.
If you convinced your company to review the policy, you would see a huge reduction in licensing to MS.
Your company SHOULD care and reward you for saving them money. If your boss doesn't, go to his boss. Someone wants to pocket that budget money, trust me.

Of course Sharepoint(MOSS) is free to you, because Microsoft gets you to buy licenses for:
SQL(server and CAL)
Communications Server(server and CAL)
Groove
and if you used advanced options in MOSS you also need
Office 2007!
And more pieces I can't even remember.

Don't forget you also MUST be on Windows 2003 server and updated AD and Exchange 2007 which requires 64bit code and thus 64bit Windows Server.
PLUS the new hardware.

So Sharepoint being free is like when you buy a dining set and get the choice of seat cushion color for free.

If it's free it's for me, but in this case it isn't free and really isn't for me....or you.

You always have other options....think about it and look into it.

Sharepoint or how a rolling stone gathers MOSS 3.0

So I attended a microsoft Connections event this morning because one of my clients wants to review sharepoint and CRM 3.0.

Let's stick to Sharpeoint as it is much more interesting.
First of all, how many people know what is involved to install this application?

The presenter, Jeffrey Lin did an excellent job. Even answered some hard questions. Did a great demo. Now the part he didn't mention, although I asked one piece of it.

You need Exchange, SQL and (I love this one) Windows Sharepoint Server 2.0!
WHAT!? Some upgrade.

Now those of you in Lotus la la land who have let Sharepoint in to your organization now have a huge fight. Exchange is now available to anyone who wants it and you can see where that leads.

All because you did not want to push the Domino products? Quickplace was/is a great product, Quickr is even better. No limitations, no giant message store.

Now I can see Sharepoint looks smoother and more professional than Quickplace but functionality, out of the box, is what is important. Anyone can pay a development house to make your site prettier.
Microsoft goes out of their way to integrate it to Outlook/Exchange and use SQL as its repository. And then there is Live messenger added to if you want presence/IM.

So again you have to add all five pieces(Exchange/SQL/WSS 2.0/MOSS 3.0/Live) and services to get what comes in 1 Domino servers with a Sametime added on one and a Quickr server.

Now here is something from a report dated March 2006 done by the great state of North Dakota. Page 5

"In addition, the cost of providing access to SharePoint sites outside of State government is
prohibitive, so it is recommended that SharePoint be available only from within the
State’s firewall, thus VPN access would be required for external users, who would also
need an AD account and the associated AD CAL.

SharePoint’s history of upgrades has not been smooth. Each new version of the product
has been a wholesale redesign without an automated migration path, and each site would
be manually duplicated after a version update."

I could not have said it better. While this is from a year and half ago, some of this has not changed. There still is not path to upgrade well. But they got the repository in SQL so that is at least better news.
WSS 2.0 was like an odd file server the way it worked.

And hey, try attaching a few 100+MB files into your MOSS and see if it stays healthy.