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I feel for you Bill. I think the biggest heartbreakers are the ones from about 69 to 78 or so. Most of the desirable cars started appreciating around then.
I have some old Road & Track mags, and some of the for sale ads just make me want to cry. Multimillion dollar Ferraris (today anyway) for 5 to 7k. Did you realize that there was one of the 63 Ferrari GTO's GIVEN to a high school vo-tech in the eary 70's because the owner couldn't see any use for such a high strung car? The last one I heard of changing hands brought something like $48 million!!!! Early Corvettes were dirt cheap. In addition to that 190SL deal I passed on, I also passed on a 56 Corvette, never hit, but poor repaint, missing the hard top. Ran and drove fine. 3 speed. Price was $700 in 1972. About that same time, passed on a 55 Nomad, then a 56. Both under $700. But, and this one really hurts, in about 1976 or 77 (first gas crisis) I passed on a Hemi Superbird for $1,200, because it had been run a little hard, had a lot of scratches.
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