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

Unfortunately the market has already tanked on your car. A 1933 !!! If you want max money out of it, pull the engine and install it in a 68-70 B body and that is the winning ticket with the money.

Those old painted Easter egg cars are a thing of the past and most people who built and gave big money for them are either dead or on oxygen about to.

My home town hosts the mid west street rod Nationsls every summer and it's been proven that people want to see muscle cars as in 60s and 70s. The old crowd of 30s and 40s are washed. Like the ZZ top eliminator, cool yes, but something people want to sink big money into, probably not in 2018/19. Every year the 30s and 40s and even 50s disappear one by one and the owners are that much older.

A Hemi super bee/ Hemi road runner, now that is a big money car that you will have people off all ages in line for.

Even A bodies are the "in" thing of this generation.

And cars from the 60s and 70s are basically "modern " cars.
Sure they don't have ABS, airbags and cupholders but they are steet-able as built.
Someone can drive them reliably coast to coast and 70 miles to work every day with no worries if properly maintained
Ask me how I know.
I just think that they will always be desired for that reason alone.
Is it OK if the Road Runner isn't Hemi car?:)