lol, you have 30 grand to spend and everyones telling you to get outbacks and cherokees? what the hell? you could get the sickest car for 30 grand. outbacks are sick, they are like the ultimate beater, but they dont drive very well and i dont know why you would spend 30 grand on any subaru. and a cherokee? for an SUV they are OK they dont offroad that great, and its like every high school chicks dream car, that, mustangs and jetta's.
if you want an awd car, for that price, maybe a newer 335xi, just as fast as an e46 m3, but AWD.
if you want something to beat on a little more you could look at STI's and EVO's. but if your looking at an STI you might as well get an EVO cause its the same price, and a way better car. dont bother with the EVO 10 or the new STI. they are watered down and less fun to drive. look for a nice EVO 9 with low miles and you will be way happier. i know STI's are the "cool" skier car to get, cause ken block totally rallies one, but the evo is such a better car. theres a reason they are so much more popular in europe than imprezas for rallying.
you could also maybe even get an RS6 for that price.
for a RWD car, id look at a bmw 135, 335, or an m3, id easily choose an e30 or e36 m3 over an e46. you could even look at some pretty damn nice porsches for that price, and you would be suprised how reliable and tough porsches actually are, they can take a beating and are one of the more reliable european cars out there. hell you could even get a lotus elise! and RWD does fine for snow, everyone thinks your gonna fucking die if you ever touch snow with anything other than awd and traction control. plus RWD is so much better than AWD when its dry.
for an SUV dont look at freaking cherokees, get something like a landrover defender, its pretty much the best offroader you can get. or maybe a mercedes g class. toyota landcruisers also kick ass.
if it were me id never spend that much money on a car, you really dont need to spend any more than 10 grand to have fun, if you have to spend 30 grand on a car to enjoy it then you suck at driving, plus older cars are almost always better drivers cars, so also more fun. there are so many cars out there that are worth 5-15 grand, that id take over alot of the cars i mentioned or alot of other cars for 30 grand, IMO the simpler the better.