[racer]

As charming as the older cars are, one thing I do NOT like, living in Virginia, is the lack of AC. The trade off for good AC (watercooled car) is the lack of charm that the older 911s have.

At your price point I'd consider
1) 997.2
2) 987.2 (mmm Cayman R maybe? not sure where those prices are currently)
3) 996TT

and since I am an IMS hater, stay away from ALL the 99-2008 engine cars, excepting the TT or GT2/3.

Even though your buddies 997 has a "new" engine, its not a 2009 DFI engine, so, it is possible even the reman motor can have IMS issue down the road, and the IMS fix for these later bad engines is more expensive than the early engines, as it requires splitting the case.

Or you could try something different - a FEWC - 928GT (not GTS, those are to spendy) or 968. Both of those have the old world charm (ride/handling/build characteristics) and modern conveniences (AC, ABS, Airbags). In many ways, they are the 964 of the 911 world... a little modern, but not too modern.