future value of classic performance cars,when to bail out, before the crash?

I hope to wear mine out bedore checking out. Heirs can give it away. No concern for $ value, all enjoyment. These are good times. USA is the top exporter of energy. Plenty of gas available, get a Hellcat for the high 50’s brand new! No doom and gloom here. It could be 1982. That was a dark time.