Tricky question really. Not sure what I would want, I have had the chance to drive a lot of different vehicles ( no real high dollar super cars, but a lot of classic cars), and to be honest, some of the stuff I had thought I'd like to own, was a big let down after actually driving it. I guess what I mean to say is, they look awesome, big horsepower, but actually suck to drive.
Even with money no object, I'd hate to buy something then find out I hate driving it, lol.
So, in the end, I'd go with a 66 chevelle SS convert., with a 4 speed, or a 70 chevelle SS convert. with an LS6 and a 4 speed.