Josh can't navigate an airport to be on WP2. People overestimate his abilities. Maybe he could have 10 years ago, but unless someone is holding his hand the entire way, it ain't happening these days.
Looks like it's a top molar giving Josh problems. The brushing probably did him no favors and knocked off a protective coat of calculus.
People are forgetting how much Door Dash fees make up Cobra's final $45 pizza order too. He is regarded with money. Every time he gets PayPal/CashApp donations, he chooses the instant transfer option; so it always takes a bigger cut of the $10 or whatever at a time instead of just transferring it all at once after an ebeg-athon or waiting 1-3 days for a no fee transfer.