If money was no object, I would like to invest in a classic musclecar from my day, to which might include:
A 1969 GTO, a boss I had used to drive one in a dark metallic green and I used to be so envious. His was slightly jacked up in the back with custom wheels similar to this one:

(The closest I ever got was a turquoise Grand Prix.)
A '70 or '71 Superbird, but these are extremely rare and the odds of finding an owner willing to part with one are just about nil:

(The closest I ever got to that was a '69 Fury.)
A 1968 Shelby Cobra might even be harder to locate, but I think it would be cool to have one:

(I'd probally have to settle for something like a Cougar.)
Any of the above cars would have to be equipped with automatic transmission as I don't have the coordination to work a clutch vehicle.
Nice!! ! You have some sweet choices, IMHO. The cougar would be a fun ride and aesthetically pleasing too.
Tried to learn to drive a stick with both my Dad and ex-husband...and realized it would be best for me to stay with an automatic too. Too many directions and some yelling almost gave me a meltdown, so gave up. Oh well...I'm okay with not knowing at this point.