I try and look at this through the lens of what I actually did with the money; it'd be too depressing if I only looked at what once was or what might have been, and didn't consider the other half of the deal.
Two years ago I sold a nice 1952 Topps Mays in PSA 5. On price then vs. price now, there's no question that I sold way too soon. That said, I used the sale proceeds to buy a PSA 2.5 T206 Green Portrait Cobb. I miss the Mays, but I'd never have the Green Portrait Cobb today without it.
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