My armchair analysis hinges completely on his compulsive spending habits and denial about WWE Champions. You have this weird self-denial where playing WWE Champions and begging for money and playing a piss-easy game so that he can vlog on Twitch is something he could do right now, and his fans would probably go wild to see him gamble on that game. But he refuses. Why? He's not afraid of admitting he's lied, and no one falls for his lie-by-omission bullshit.
My theory is that he has some amount of self-loathing about the situation he's found himself in. He probably *wants* to resolve that, to just stop lying to everyone and do what he's already doing, but publicly. Just start playing WWE Champions publicly and the whole incongruence goes away! But he can't, because that would mean admitting to himself the reality of his situation. He has a deep shame for his spending addiction, to the point where everyone but him recognizes the ridiculousness of the situation he's in.
He needs to learn to accept himself. That'll make him happier in a thousand ways, but resolving this incongruence between his on-stream persona and the shame he has playing a gatcha game about sweaty men to save his income is probably high up on that priority list.
A lot of his life can be summed up with two thing he doesn't have: Drive and Impulse control.
For all of his publicly documented life, he historically only cared about one thing: Going to the fighting game tournaments. To the point that it put him in crippling debt (that he happened to luck out of because of his newly discovered YouTube windfall). He only got jobs because daddy said "Get a fucking job or get the fuck out" (it's a common tactic for parents that try to sack up, but it almost always lacks teeth). When he couldn't hold down a job, daddy stepped in again and said, "work for me. Keep your mouth shut and do what you're told." Even that wouldn't work.
Then YouTube happened, and he liked how it tasted. He could lay on a couch, point a camera at a tv, and he got paid for it. Paid well. Stupidly well. More money than he'd ever know what to do with. Now any smart person would tell you take what you don't need to survive and invest that shit and live frugally. That's one way to do it, but I don't buy into the whole idea of slog through 40 years of work in the hopes of the possibility of enjoying some of that money you hoarded at the tail end of your life, if you even make it that far. But I also don't advocate spending every fucking cent you have, it's like he has an allergic reaction to money, when he has it, he has to get rid of it. But Phil saw all those zeroes and looked his dad square in the taint and said "fuck you dad, I made it."
And then immediately spent it all.
But that's okay! More kept coming! He kept shitting out videos and money kept coming in. At first he didn't get it. Then he put it together: He's got the personality for it. He's a natural presenter! He's the Rock Fucking Hudson of YouTube! And so for a time, this worked. He would vomit out videos at an alarming pace. Money came in, and he'd buy whatever he wanted, the second he wanted it. Toys? Done. Car to never drive in? Done. Constant take out? Done. Condo to fuck broads in? Done. So now he's got tonnes of debt, few actual assets, and a finite income.
I could go over the whole decline and the engaging with trolls and then the sudden recoil from trolls, and how he fucked himself over again and again and again, but it's all on here.
At that point it became the game of path of least resistance. His income was dwindling, and instead of finding ways to increase his income, he tried to find ways to lower his costs (which is fine, don't get me wrong, either one works). He googled which states have the lowest income taxes, picked WA, and stopped looking into it then and there. His 'tax attorney' in CT said "hey buddy, keep forking over that cash and I'll keep you covered over in WA, too." Phil, already rubbing his back from all that googling gave him a thumbs up. So instead of dealing with his property in CT, which, to be fair, was a hefty kick in the balls for him with the crash, packed up and fled across the country. In his mind, not having to pay as much income tax would mean more money in his pocket! The problem would fix itself and he could go back to the way things were. A no-brainer!
But they didn't. The downhill trend continued, but so did the spending and the habits. He tasted the good life and going back just wasn't a thing he was open to. He had to keep his hoard, without giving up a single thing, while not changing because he wasn't the problem.
And now, that trend has put him exactly where he is today, massively spending every single cent that comes in on himself, bankrupt, losing the condo in CT, lying to a group of people that have maybe a single brain cell to share between the lot of them, failing health and body, a marriage that's been bleached of anything resembling affection and is more a pact based on mutual destruction/survival.
Behold: The successful business man, with an adult business degree.