I'm just gonna go to the track whenever I want, with whoever's running. When I raced with the POC, I would also do their time trials and slaloms. They had (IIRC) the "Red" group, which was open passing, and a lot of the fast race guys were in there, with either their race cars, or flogging the wife's car. You could race door-to-door, stuff people, whatever you wanted to do, as long as you didn't put someone in the weeds, or ram 'em. I have considered a used modded up car. I'm supposed to look at one Monday.. You do have to be careful that with these cars you could be buying someone's problem, and/or one that's just been wrung out for too long, especially with the 911. Their pan just doesn't hold the stress or g-loads after a while, and you end up seeing a lot of repairs to it.
I like the new car idea, because I'll know I'm the first to use it, and the reliability will be there. I don't neccessarily want to mod the piss out of it. I want to start with a good baseline, and then change what I don't like. I don't want to re-invent the wheel with it,though. Both the Cayman and Evo fit this description, and I'm sure I'll be happy with either. I just have to remember that someone else will want to enjoy the car as well. Track-only suspension, and a triple-disk clutch for instance, would take away from the experience for my wife. An Evo with an HKS BOV, aero kit, and 12 gauges on the dash, would definitely not be something she'd drive.