For me it has been mostly luck and a lack of much caring about condition.
Both T206 Cobbs I have were $50 each, but are beaters.
The big names have always been a bit expensive, I really should have bought more 50's and 60's stars back in the late 70's. But to me, they were not only "expensive" (Hardly any were even over $50 when I started) But seemed to be pretty much available whenever I might decide I wanted one.
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