Hey Mark,
First off, in the end, they are only cars. With that in mind think of what the future could bring. If you lost your job again you may be put in a spot where you would need to sell them just to survive and then you basically have nothing. At least with a business you are creating your own destiny and opportunities. If your successful you will be back in the car world as its your passion, if your not you will have no regrets as the biggest regret is to not try in the first place. Just remember, owning your own business is 24 hours a day and starting one from scratch will feel like 48 but the rewards far outweigh the risks, Ive been there and have built 3 pretty successful companies and that took alot of time and effort, still does, but these days I can do pretty much what I want when I want. The cost of the cars is only relevent, when I went in the direction you are thinking of going back in 1982 a 69 Z was about 5K, now their 30-50K but I can get alot more today than I could back then and if I was working for someone else I might not even have one anymore, who knows you may wind up being the next Bill Gates and be in a position to have anything you want, you never know until you try...Good Luck and remember, there only cars.