Out of what you mentioned id choose an EVO, better than the STI in every way, more reliable (if it hasnt been modded, which goes for all 3) S4 will have the best AWD system and perform the best in snow, but the B5's are the opposite of reliable, and the b6's (v8's) kinda just suck, i've driven a couple and they did nothing for me.
s60r's look cool, i know 2 people that have them, ive driven them, they dont drive very well, sure they're pretty quick, but they just arent that fun to drive, didnt like the AWD in the snow either.
R32's are pretty sweet, ive driven the first gen and the most recent, the first gen was MUCH more fun to drive, way more involving, one of the most fun cars ive driven actually, so good for just cruising around town and stuff quickly, feels like a go kart. they start to suck once you push them though, and their AWD system blows.
check out the e60/e61 535i, if you can find a 535i touring in a manual you've found one of the coolest cars ever. or the 335i if you want a 3 series. They should be getting down around your range by now.
if you want to go audi, check out the c4 s4 and s6, id personally go with an s6 avant cause wagons are sick. they're pretty damn quick, and will easily match an STI, EVO, newer S4, etc.. with pretty minimal mods, and they'll do it reliably. The shop i used to work at saw a bunch of audi's, subaru's, and other imports, those late 80's to late 90's audi's are fucking tanks, you'd see them get over 300,000k miles and keep on running hard with basic maintenance.
Honestly, out of all the cars ive driven, sti's, evo's, GTR, lots of audi's an vw's, a bunch of super modded shit, i still think the most fun ive had is in the cars like stockish miata's and e30's that just give you a basic, raw, connected feel, and are much more involving. so those are the kind of cars id recommend.
