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Hi:
1)You can drive almost any car in the winter, if you have a set of snow tires, weigh down the rear axle, and have experience driving in snow. But, the Boxster is at heart a sports car, so it will never be like a heavier sedan or SUV in snow; that's not what it was built for.
2) No way doesn the car lose any appeal in the city; just whip around those corners dude!
3) Best time to buy a sprots car is in the winter. Simple question of supply and demand. Less demand in the winter for sports cars.
4) Tough question. Someone summed it up nicely earlier. Newer models are a bit nicer, and faster, but more money. Just depends what you're willing to spend.
5) I would recommend staying away from 16" wheels in olders models. Also, get a 2003 or newer if you can; the plastic window I have is lousy.
6) I've owned 3 series Bimmers, and I currently own a Benz C32 AMG as my everyday car. Go and test drive a Boxster and see what YOU think are the pros and cons. Bimmers are nice cars, but I've always found the seats to be less comfy than the Benz, but the car is definatly more driver oriented than the Benz. The Boxster is a pure sports car, so you'll find the handling to be even tighter, and more of a bumpy ride than your 330ix. By the way, nothing like 4 wheel drive in the snow. If you want a Porsche in the snow, I'd go for a Carrera 4S.
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