Think about it, ever since summer right before his little staycations he had an issue to deal with, these all line up with the dates she visited him or around that time, Phil's tax situation is either to scramble to pay her back resting on the fact is Christmas and people are more generous. He also dropped a lil tid bit about his health but didnt go into it because health is a last-ditch effort for pity monies which he will jabber about during his Christmas marathon streams.
He didnt wanna pay her from Twitch and You Tube money he wanted to pay her through tips since tips are straight cash delivered right to him with at most a few hours wait for a bank transfer. He didnt wanna use the money he "earned" through twitch and yt and teespring, he wanted his fans the ones he hates to pay for this. He also had a nice little prescription bottle in that video of his walkthrough and didnt bother hiding it.. why? Because its gonna be brought up soon.
Taxes= Escort, Health=Escort, Condo fees= Escort and all that goes with a visit (going out to dinner and airfare)