Nicely done. You did an admirable job, and you learned a lot because of it. We all have time pressures though, and so we usually end up going back to our comfort zone.
To comment on your points:
1. It is absolutely frustrating to get very close to usability, and then hit a roadblock. It drives someone nuts. Here are my thoughts on your utils:
1a. Live writer - no experience with this, so I can't judge. When doing some research for you, it seems a lot of people love the program. Who would have thought a cms for a blog would be a killer app?
1b. Word I'll come back to in 3.
1c. Tried using sketchup for a quickie model, and it is a relatively nice tool (although freebie has some deficiencies with curves that drove me nuts when modeling a wavy line). It didn't work in wine, and I know that they are working on a linux port, it's not out yet. I used it in xp, and it was pretty good. Wouldn't pay $500 for it, but I can see how it would come in handy for its extremely intuitive interface.
1d. Don't love thunderbird, but I set up a free zimbra server at work, and zimbra desktop is great. May want to try that out (it works on all platforms).
2. That's what happens in the early goings until you find "your programs". I kept trying kdenlive (an editing program), and kept finding little things that caused issues (likely due to running it in gnome). Now it has come of age, but it took a while. Some of the core programs are very close to being time savers, but some of the niche programs are just not there yet.
3. I see you are collaborating, and that is the problem. The issue is that Word has it's own issues (bullets are way easier on OO.o), but since everyone is using it, it is entrenched. I had a vba macro I just converted to OO.o (it writes my quotes based on a spreadsheet), but some people just like their old macros that still muddle along. What kills me is people who tell me I have to pay a ton of money for a software suite (or Cad program), just so they can see my raw doc. If you can make the changes, they can use OO.o for free. I knows, I'm living in a dream world.
Linux rocks the server. I was running our email, web, file, and print sharing from the bosses 8 year old computer he was going to throw away, for 3 years before it finally died of old age (likely due to the lack of ac that the boss turned off over the weekend).
I think I know what you are talking about with the files - ubuntu has an issue where the shares don't always show up on a search (happens in pc's too, so I just map). That killed me on my laptop, but I found a fix, which should be in the next version.
Here are some thoughts on linux:
1. Release frequency - With ubuntu, I get an all new version every 6 months (debian is longer, so it is better for servers). I don't have to wait years for usability fixes (usually).
2. Security - Do I even need to go into this? No AV makes my 5 year old laptop fly when it dragged in windows.
3. Updates - any packages that are installed from repos get updated. Almost every other day there are updates for all the programs I installed. No looking around - critical errors are closed, and I don't have to worry about 10 little programs in my tray warning me about updates. And did I mention not usually needing to reboot (and soon never needing to with the new splicing program).
4. Choice - Lots of programs to choose from, lots of ways to get involved, and if I don't like something, I can fix it myself.
5. Cost - the only cost is time and energy. Which I know you have put a lot in, but it does tend to step down as you get comfortable.
Finally, some good points are made here:
Helios - Charlie Brown Windows Users
Good luck in the future. Please try again in another year - a LOT changes that fast in the linux world! (including the new mythtv .22, which should blow media center out of the water - and .21 is pretty close)
