I switched to Debian four or so days ago, and it’s kinda making me feel stressed. I’m having to put a lot more work into the operating system to just make it work.
Firefox for instance – oh, sorry, Iceweasel – took a lot of Googling and about:configing before it felt the same as it did on Windows. Why some of those keys and things have changed is odd for me. Why has ^J for the download menu suddenly been switched to ^Y? Why use Alt instead of Ctrl for tab manipulation? Why doesn’t clicking the address bar auto-highlight it all? These just seem like weird changes to me.
I’ve installed a few extensions in Songbird. It says they’re installed but there’s no other sign of them. No way to run them. No obvious way to get to the iPod functions which apparently exist…
I’ve no idea what I’m supposed to be installing to get OpenGL to work. I need it to play Eve… (Which is apparently no longer in development…)
Installing things is also a little bit of work… I don’t know why more things don’t come with a set up wizard, like I’m so used to in Windows. Instead, I have to try and remember the switches for untaring things, putting them in the right place. Sometimes just guessing what I should be doing to run the damn thing.

This just isn't nice... It looks like it can't decide on what width to use for letters sometimes. Blatant attempts at adding extra pixels to make it more round.
Fonts are a weird, picky problem for me too. But I think that’s just because I’ve not played around with the defaults enough yet, to find one I actually like. Needs more anti-alias, and better kerning.
On the installation for Debian set up thing, I asked it to install a web server. That may exist, but I’ve no idea where to find it… My PHP pages aren’t giving me any errors, they just don’t seem to be outputting anything at all.
It’s just not new user friendly. I’m hoping that Ubuntu is much better in this domain, since that’s what it’s designed for really. So, I may be switching back to Windows some time soon. I don’t think my life can handle not having it as a primary operating system just yet. In the furutre though, I’ll defintely be installing another Linux OS on my next machine.
You really should give Ubuntu a try. I love Debian to bits, but even when I used Debian all the time, I prefered it for servers and something else for a desktop.
The latest Ubuntu 9.4 will be out in April, maybe wait until then rather than installing 8.10 now.
I’m rather liking 8.10 myself, very easy installation everything is setup. Even the proprietary nvidia drivers are available (and iirc offered to you after the first boot) after ticking a box and rebooting.