I have a few that I would not mind having again. But, money is money and cars are cars. They can be replaced by something someone else has dumped cash in for less then you sold your old one for in some cases.
Good chance if you did find that cherry ride you have had years ago it has been rode hard with most of the cool stuff replaced. ie who drives a big block as a daily anymore good chance there would be a smaller engine in there now etc.
I had a 1991 Pontiac Lemans 2 door 5 speed that I absolutely loved the entire 4 months(That was a long time for me to keep a car back in 2000) that I had it. It had a throttle body spacer and I had a buddy flash the computer. I drove the thing over 10k in that 4 months driving down to Memphis and back. That was one of the few cars that I never got pulled over in despite there being a few moments I was expecting to.
Looking back at it the car was eh ok I guess it is still better then most new cars on fuel mileage. It is more about the memories you have not the car itself. Some of my best memories are in total POS that I ran for a few weeks then derby'd afterward or gave some body work or a zap, check, fix and sold for a small profit.