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If I lived where it got stupid cold, I'd be sure to get a Boxster with a glass rear window (which includes a window de icer.) If I lived in the salt belt, I'd probably look somewhere that's in a different region. Salt is tough on convertibles--I once had a bug convertible that the top frame was pretty stiff from rust (and other places were corroded out.) I'd look in another region than the upper midwest or upper north east. My 01 has a more than adequate heater/defroster/AC. I wouldn't hesitate to drive it in cold, snowy weather.
Some general rules it seems to me. There's NO such thing as a cheap Porsche--if it's cheap, it needs work. If you can't do the work yourself, you're at the mercy of expensive technicians. And lots of things can be wrong. I can do my own work, and I was very tolerant of having to restore my Porsche. But knowing what I know 4 months later, I wouldn't have bought my car.
Good deals are not season dependent. If you do the research, you can find deals that aren't outrageously spendy. If you're willing to have the car shipped or you can go get it, even better. If you fly, buy, and drive, have it inspected and serviced before you start back.
Do your research on what the designations mean. A Boxster S has a bigger engine, and fancier stuff on it. Heavier tho. I have an 01 Base, and I kinda wish I had an 01 S instead.
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2001 Boxster
2007 Toyota Highlander
2003 New Beetle Convertible, Turbo, Tip 6 speed 
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