Older Turbo or newer 996

[ccm911]

I am seriously thinking of upgrading my 1984 Targa to a different car next year, and have kind of focused on two possibilities.  As I am not planning to take the car to the track, I would be more looking for something to take out on the weekends for the occasional beating.

I am thinking of the following:  Buying an older, well maintained Turbo, or buying a 1999 or 2000 996.

The Turbo really sounds fun, and I think that prices have stabilized enough to not punish me when the time would come to sell.  But...the 996(even though I hate the shape) would be newer, and a heck of a lot more comfy for some longer distance highway sprints.  But, if the car was like $75K new, and is down to the mid-twenties now, would I lose a ton of money when  went to sell?

Tough, but fun choices.