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Here is my few cents (I live in Waltham so I have been through that)
1) And most important! Car must come from a person with a garage (even better two garages), who has an SUV or something to drive the winter. As you may know all cars become junk around here because of diving on salted roads. Make sure that the owner loved his Porsche.
2) I would say don't mind the stereo, buy something without heated seats (it's a guaranty that the car was not driven in winter). What ever stereo option Porsche has you will find yourself wanting to upgrade to an aftermarket (GPS head unit, better amp, new speakers...)
3) If you can get an older Boxster 1997-2000 with a 3 spoke wheel, clear headlights and rear compartment. Go ahead and buy it. To me it means that the owner loved his Porsche.
4) The most expensive mods that you would like to do are: larger wheels (18" at least), 3-spoke wheel and headlights. The price to do these competes with the price of an older Boxster (ok ti doesn't :-), but these are extremely expensive compared to the price of the old Boxster).
Except for the wheels I just described my Boxy :-))) .
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