I could have sold my 1952 Topps Mantle (PSA 1) and Goudey Ruth #144 (PSA 5) for quite a bit more than what I got 10-12 years ago if I had held onto them a few more years, but I needed the money for other things at the time, so those don't hurt too much.
It hurts more when I sell a rare card. In that respect, I guess the (unique) Mino Bridwell stings more than the other cards I've sold. What I decide to sell is largely a function of the price/rarity ratio. If I ever acquired a T206 Wagner I'd probably divest myself of that one pretty quickly.
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