Buy new unless you found 1 in extremely good low mileage condition but then those are usually kept by the owners cause why loose money on selling such a mint car, but if I was you I would also look at preowned 911 Turbos, 50k can buy a lot but you could remorgage the house with what performance upgrades cost, Corvette is best dollar for performance value on the market and small things increase power the most, just ask any Corvette guys, advance the timing just gave you another 100hp, silly stuff like that.
If you can do it buy new, it's yours and you know from the get go whats the deal plus if your gonna keep it don't worry about the value, mod the hell out of it and take it to the track and find a corvette club, go with a brand new C6 and know that that basic body style will be around for 5-7 years no doubt.
The Insurance should not be to bad, I priced 80k cars and for full covererage was an additional 400 a year, my record is clean, remember it's a second car in your name how the hex can you drive both at once, and if you live in snowy areas then you can even insure it for 6 months.
You only live once
