Another thing to consider is having 2 cars. By buying a second car that depreciates less (it's cheaper, older, etc.) you actually save money. And with 2 cars you can go no-compromise on both ends of the spectrum.
Recommendations: E39 M5, E60 M5, C5 Z06, 996 911 GT3 or TT, Ferrari F550. Second car: Honda Odyssey, Honda Accord
The point is not that GT3 is a frugal choice, but that buying a new car is an extravagance, and for the same cost you could be driving a vastly better car.
4WD is, of course, nicer. But I don't want people to think they have to have a 4WD vehicle if they live in a snowy place.
Four wheel drive is great for a lot of reasons, but in the winter it's only real benefit is acceleration - getting you unstuck or up hills. You're not less likely to crash while moving in an S4 as compared to an M3.
Now, on the track, it makes a BIG difference. In the snow, however, your goal is safety... not competitive times.
Even four wheel drive won't do much for you if you enter a corner too fast, assuming you don't have a rally driver's skill set. Control requires traction. Traction comes from tires. Get appropriate tires for your driving conditions.
That's the reason I'm about to get a new car - I'm moving across the country, I don't know any of the possible sellers or any of the area mechanics or dealerships, and I really don't want to deal with all the car maintenance stuff on top of all the other stuff that comes with living in a new area. Otherwise I'd buy used. And I run cars into the ground - I expect to get 10-15 years usage out of this one.