[onewhippedpuppy]

You are always going to lose your ass buying a newer car. It gets even worse when you consider depreciation, maintenance, insurance, etc. I would recommend buying something in the $20-40k range, which will yield a nice 996 or 997. Why? These $100k cars have by this point already lost 2/3 to 3/4 of their value, and the depreciation curve is starting to level off. Because they have lower book value they will be far cheaper to insure. As for maintenance, you can find a low mileage car that won't have much more than a brand new one.

Another option would be to go older and buy an SC or Carrera, which seem to be increasing in value, a 964 which are bargains right now, or the 993 that seem to have bottomed out at $30k. The older cars will require more maintenance but will all likely appreciate given time, and can be cheaply insured with a collector car policy.