Im about the same age as you in a similar situation. I have alot of the same feelings as far as wanting a nicer/newer car, but at the same time I see my friend who has a $300 a month payment and there is no way I would want to be tied down to that all thru school.
Even though I buy alot of shit for my 240, my total investment is still under 5k. It might not be the newest car or the best platform for a track car, its still fun for what it is and gives me a relativly cheap DD for the summer.
Its very interesting to see how much money you can really have when you live cheaply. the same friend I have with the $300 car payment works full time for ~$10/hr and I would say I have just as much spending money as him making $120 a week.
And as far as the GTI being bad in the snow? I see people all the time in buff state parking lots with rusted out 92 tercels with completetly bald tires and they seem to get around just fine. It kind of seems like you are using that as an excuse to justify the evo