[DGriz]

+1 with Charles regarding depreciation.

Buying a new exotic that depreciates quickly is actually losing you money. Buying an older, pre-depreciated 911 does not. You may have lost the opportunity to invest or spend those funds elsewhere, but after 20 years you may likely get it all back plus some.

Also consider the "bang for buck" discussion. A buddy owns an early 80's Alfa Romeo Spider as his 3rd car. He has a beater 200,000 mile Suburban for hauling and ski trips, and a new Mercedes sedan for his business "appearance" car. We can knock all three for various reasons, but he's said many times that the Alfa has by far produced the greatest enjoyment over the past 10 years for his paltry $5000 investment in it.