I have normally been using my WinXP system and now dropped that dead machine for my ubuntu system. Here are some things that windows users might look for. Cot oriented review. Been about a month and a half since I was fully on linux desktop.
1. Everything is free, opensource. Using the command "apt-get/apt-cache search" will get most software you will need. I did do one manual install for the cool editor komodo edit. That was about it. You normally have to do apt-get for software that you need at the time as opposed coming up with some long list. I recently installed Rhythm Box for music (I guess a windows media clone, hahhahaha)'
2. Installs and Package manager (see above)
3. Eclipse Europa, great for development. Same as Komodo Edit.
4. The console
6. Ubuntu Forums
7. Ripping songs from CD to filesystem is simple with tools like Sound juicer (stick in cd, rip and you are off. Think format is ogg?)
8. Open Office. Nice tool, you need ram though.
1. You have to get a top-notch machine for the same performance on a winxp machine. Don't listen to LoB, for linux on the desktop to work, you probably need something beefier than your win box. I have a AM64/3.2ghz/1.5gigs of ram and Nvidia card/some creative labs sound card. I would NOT get an ATI card (or anything card for that matter). Anything else will probably run slow and clunky
2. Most of the desktop software seems amateurish (but that is ok). I mentioned Rhythm Box, which is good but is at a 0.10 version. It works, but looks like they spent a week on the UI. Not that polished windows media player. I think the same can be said for Gnome in general. Seems like either the font is too big, or too small. Too much anti-aliasing, too fuzzy. It works, but just not as polished.
3. Sometimes Buggy. With XP, I have been ok with closing volatile applications in the task manager. With linux, applications can lock-up and you have to search for the PID and all of that mess and still may not close the application. And little things, like desktop icons move at random from where I expect them to be. Crap like that. Sound may or may not work (and I am using same card from windows system)
4. Desktop configuration settings. Console settings are easy, but sometimes settings don't to get carried over to the UI because of some hidden Xwindows/Gnome setting, just pain in the ass.
5. Media is hit or miss. I am sure you CoT people are into porn. Well your porn may or may not work. Youtube works (with simple flash media plugin). avi/mpegs may not, depending on where you get your codecs from
6. Gimp. Would these developers should move on to other projects already.
7. Manual installs of software. Still can be a pain the ass. Do I have libcpp6/5? What version of gcc? Do I have all of the dependencies. With apt-get, it is easy. If the package you want to install is not in the ubuntu database, you may have to become spock to figure out how to install software.
Basically, I don't think you will have too much problem moving from WindowsXP/Vista if you are looking to do so. I might recommend putting your files on some fileserver and copying them over. Me, I had several years of docs/projects I wanted to finally move over and most of them were moved and I could open them open the various linux software (open-office, etc, eclipse).