I also have a 997TT. Fun car but, not as practical as the Cayenne.

It sounds like you enjoy your 955T. Id keep that and if your garage has the room, get the second car. The 997TT's are at the right price now and wont be seeing dramatic depreciation.

I wouldn't get the R8 4.8. Although affordable now, you'll want to supercharge it and will have difficulties on resale due to the V8. (Just my opinion.)

 

How reliable has your 997TT been? Right now, I think 997TT prices are a too high. I'm hoping as interest rates increases demand will fall and I can scoop one up at a good price. Its hard for me to pay 70k+ for a used 997TT with 40k miles on it when just a few years ago a 20k mile car was bringing that.

 

997 has been great. I push the car to its limits and, it proves itself over and over.

I lost a turbo last year but, beyond that, car has been solid.

As your post states, cars are not an investment by any means but, if I sold mine today, I would have lost 6k on it over 3 years while maintaining a stock state. I dumped another 30k+ on it since.

I now understand the "slippery slope" statement.