I HIGHLY second what Uberlord said.
If I were the second person to post in this thread, I would've said Ubuntu as well, seeing as how it is very user-friendly.
But considering your situation now, I would move to Gentoo. It requires actual BRAINPOWER. But it was my first Linux OS, so it's not as hard as some people make it out to be.
It also doesn't base itself directly on releases (as portage, it's update software, ALWAYS updates to the latest stable version of EVERYTHING), so compatibility should not be as big of an issue.
Most of all, the support forums are absolutely amazing.
Check it out for yourself,
http://forums.gentoo.org