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

The two things we are sometimes arguing over here is 1. The $$ part of it all, when to sell and not sell at the bottom of the cycle 2. Enjoying the hobby and caring less if the car becomes basically worthless.
It costs basically the same $ to restore say for example, a 69 440 Charger RT as the 65 Dart slant car, EXCEPT the cost of the initial project! Pretty much the same for body/paint, mechanicals, exhaust, tires, front end work, interior! Yes the project car costs would be like $1500 for the dart and $9000 for the Charger, but the Charger with a full blown nut and built resto job , that car would bring maybe $40,000. Maybe $50,000 at BJ? What would the Dart bring in like condition? maybe $5000? Now if the owner can do the resto himself and not pay for it done, he could make a profit n the Charger, but the Dart? No way. He loses maybe $15,000-20000 Now if the owner mays a high end shop for the resto , he is out how many BIG one!!!!!!! $80,000? for either car!
Good thing most all of us are into this for the $$$$$!!