I've never had a "fast" car before. I've always just wanted a car that drove as nice and smooth as possible. I have started looking at older 911s though. Older as in 2000 or around there. I want something fun to drive and also something to work on. I've found in the last few years that I enjoy working on cars. When the wife and kids go to bed at night I like to have a beer and mess with the car. I don't however like messing with one that I rely on during the day. So if anyone knows anything about 911s let me hear about it.
With a 911, be prepared for insane, tight spaces to get a wrench into - you might need some "foreign" tools and you'll obviously be working in what we call the trunk of the car. Dealing with foreign parts is a pain in the ass, yet if you have an SS in the garage and need an alternator, just go down to AutoZone or Advanced Auto and get one.
If you want to go as fast as possible and mess around with it in the garage, get a grand national.
I will have a porsche someday - but only for a couple of years until I get it out of my system. I plan on buying one and selling it before my kids turn 16. Also, I will never in my life work on another car.