Welcome to the Forum -
I was in the exact same boat you're in not too long ago. I was pricing out several different options but always had my heart set on the Boxster. I managed to find a low-mileage one which, for the year I've had it has seen 20k. It is my daily driver every day of the year. You'll notice that I live in Toronto, where the climate is not at all unilke that in NY. If you don't need the back seat and can deal with the abundance of trunk space (compared to something like a BMW Z3 or Z4 then I'm sure you'd be happy with a Boxster.
I suppose what it all comes down to is what you consider "fair priced" repairs. I have had nothing but scheduled maintenance, which has been wonderful (albeit rather pricey in my own opinion). That said, I haven't had any other problems at all, and would highly reccomend it any day of the week, regardless of snow/rain/sun (basically any weather condition). My reccomendation would be to find a low mileage post-model year 2000 since it seems that previous years experienced more "kinks". Also, a base Boxster is just as much fun as a Boxster S and it can save you a good deal of money when buying one. Oh, one more thing, the hardtop comes in handy in the winter thanks to the defrosting glass window.
I always say where there's a will, there's a way!
Good luck with your search!
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