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I know people aren't going to believe this, but honestly, you don't need to be a bazillionaire to collect vintage cars. It sure helps (a lot!!), but depending upon what he was collecting, you can buy certain classics for (relatively speaking) cheap.
The director at my old company was into classic cars too and we would shoot-the-shit all the time about his cars and mine.
My whole family was into vintage British roadsters. If you're willing to work a bit and to flip them after you've had your fun, all but the first one pay for themselves.
But it's hard to say goodbye!
I always thought of it like sending my kid to college. Doubly so because the money I got from selling my '72 MGB sent me to college.
I always think of it like Pokemon. I want to collect them all.