I really doubt there's a double taxation problem or that if there is it's anything to lose sleep over. Most non US countries' taxation departments are a lot less punitive, way more friendly and more likely to assume you just made an honest mistake unless you rub their nose in overwhelming evidence of the opposite. Now what Andy perceives it as, given his cognitive abilities is a very different question
He is streaming it because he's an impulsive dimwit, who may actually be borderline exceptional, and who talks about anything that pops into his head for 4 hours a day for a living whether there's anything to talk about or not. If there was a confusing $5,000 mistake in the bank accounts, it would more surprising if he kept it to himself
Andy seems to use the terms agent and manager interchangeably. Based on him saying x % goes away to the manager for each performance of the show, I would guess the person acts more as a talent agent rather than a business manager