not sure how to define weirdest so let me pull something from my level 5 mini infodump drawer:

pachinko parlors in Japan can't cash you out, because legally speaking, they are not gambling places (and in general casino gambling is currently illegal in Japan). however, they do offer a whole bunch of prizes (just like an arcade) with a defined upper limit of 9600 Yen per prize (£46 now).

however, when there's a limitation there's always legal shenanigans -- those pachinko parlors will happily give you "special" prizes -- normally a tiiiiiny piece of gold or rare metals encased in a plastic card form, and for some reason, there will be third-party shops called "prize exchange shops" near those parlors more than glad to give you cash for those plastic cards.

but wait, we are not done here! those "prize exchange shops" would then sell these cards to ... another shop that is licensed to buy/sell second-hard merchandise, and then finally the pachinko parlors would buy those prizes again from those shops... it's a giant legal loophole