There are desks at banks whose entire reason for existence it tax arbitrage. It's not really a great use of people's education and time, but it's real and it's legal. I don't know the specifics of how it's done, but I do know these desks exist.

There was another case in Denmark where the tax department basically neglected to check that the claimants actually owned the shares and just sent them a huge amount of withheld dividend tax.

The underlying issue is that the rules can be gamed, but only by entities who can pay for the professionals who understand them. There's gotta be a smarter way to arrange the tax system.