Also: how well does Wine work?
Its compatibility list is a bit weird. It's kind of a hit-or-miss thing.
From what I hear, it'll run Steam and HL/HL2 with a bit of work. It runs WoW. Neverwinter Nights, from some accounts, runs better via Wine than with its native Linux version (which is kinda sad). IE6 and Office 2003 both work (I've used Word, Excel, and PowerPoint extensively under Wine, though some Office components don't run well, if at all).
Your best bet would be to check the
application compatibility database on their site. Also, bear in mind that some games, like the Quake series and the UT series, have native Linux ports available. I've played Quake 1, Doom 3, and UT2004 extensively under Linux and they run just as well as they do under Windows.
SKETCH BOOK RAPE.
SAVVVVVVEE MEEEEEEEEEE
NOT AGAIN :O