When it's being used as a money launder scheme, someone does get stuck, but it doesn't matter:

"A" makes a painting. "B" buys it for $1000. "B" then gifts the painting to Dickish "D", who is trying to launder money. "B" THEN pays "C", an "art Critic", $1000 to say the painting is worth 5,000,000. "D" could also do this step, skipping "B" entirely, but obfuscation is nice to have. "D" now sells the painting to an Enterprising "E" at "market value". This is where your scenario stops: "E" never pays "D", and is some $100 numbered corporation that just dissolves into thin air, but "D" notes that the laundering-needed money came from "E", and now is a legit source of funds.

But the more advanced version has "E" be a large megacorp, easily able to eat a 5Mil purchase. "E" then has their own appraiser re-check the value of the piece, since it has appreciated so much in such a short time already. Wow, wouldn't you know, it's now valued at 25Mil. Now, this WOULD be a problem, since you need to recognize appreciation of assets as income when realized... But it is never realized. Instead, it is donated to "F", our Final stop, a hospital or a university, or even a political party, that is a registered charity. "E" is down 5Mil, that's rough. But it just donated 25Mil to charity, lowering their income by 25Mil (and their tax burden by about 5Mil), AND gives them a charity deduction of ANOTHER 5Mil off their tax burden! By buying and ditching that worthless piece of art, their coffers are 5Mil heavier.

The non-profit, of course, has a painting probably not even worth the original $1000. But it got it for free. Source of funding, plus 25Mil... But they're a non-profit, they just raffle away the painting for a piddling fundraiser amount and mark down the loss.