You could say the same thing about classic cars, watches, anything. And wouldn't we all like to find that "once-in-a-lifetime" deal on the perfect set of chips, the most beautiful classic '57 Chevy, or the Omega Speedmaster that Neil Armstrong wore walking on the Moon?
Excellent and informative post all around. And yes, I
am saying that, except in the instances cited above where there’s some kind of asymmetry (knowledge, financial situation, generosity, apathy) between the two parties in a transaction.
You’ve reminded me of a friend (who FWIW is a truly terrible poker player) who used to make a ton of money from a venerable family business started by his dad. He was an extremely loose spender (e.g. holding lavish champagne parties, putting way too much money into his house, etc.) and did not pay attention to the clear warning signs in his industry which should have told him to evolve, or sell before the bottom fell out.
Long story short, he went bankrupt and lost everything but the stuff he had accumulated during his loose spending days: a big cellar full of expensive wine, some fancy furniture, artwork, a vintage Mustang in perfect condition, etc. To raise cash, he sold this stuff off either to friends or via an auction house. A neighbor got a truly beautiful 100-year-old pool table in perfect condition for about 15% of its value off him... I had expressed strong interest but he “forgot” and “got impatient” and sold it for much less than I would have paid. Though chagrined to be selling stuff for pennies on the dollar, he was as undisciplined about liquidating his remaining assets as he was when he was making hundreds of thousands of dollar annually without hardly lifting a finger.
Few people felt particularly bad for this guy, because he had been so ostentatious and careless with money before. I actually loaned him a few hundred bucks when he hit rock bottom, fully knowing I’d never get it back even if his finances recovered... It was more to honor some shared history, and also to get him to stop hounding me. Cheap at the price.
Point being: There were real deals to be had from this guy. I didn’t buy much from him except knick-knacks—we don’t have similar taste. No doubt it was exploitative to buy higher priced items from him, in a sense, except that he had (a) eagerly dug his own hole and (b) didn’t seem to care even when things fell apart. (He fought the lenders over a foreclosure and managed to stay in his house for free for nearly a decade, until a court finally ruled against him.)
Now he goes around reminiscing about how rich he once was, and seems to derive almost as much pleasure from that as he did from being wealthy... As far as I can tell, he lives off his military pension, social security and the modest proceeds of his liquidation, and ultimately does not really seem more or less happy than before.
Unfortunately, he owned no vintage poker chips.