This implies that donated art basically has an arbitrary valuation (set by "experts" based on some not really free or transparent "market"). Is this true? How is this handled for other assets?
If Pierre's paintings are being exchanged regularly by a bunch of hedge fund guys for $20 million each, isn't $20 million the market price of a different, arbitrary, painting from Pierre?
It isn't really a problem for other assets because they don't have the museum donation market that's key to the scheme working. You can't find a charity who is looking for superyacht donations.
Not at all: to have a "market" you need buyers, sellers and goods to be fungible.
In your example buyers and sellers are only 0.000001% of humanity: other people cannot afford to play this game.
Also the goods are unique. Brand new paintings would not be sold by the author him/herself at that price 99% of the time. They skyrocket in value only when sold between billionaires.