It made sense before the bankruptcy with all of those credit cards and all of that interest (most of them nearly 30% interest so he was likely making minimum payments covering the interest but the balance was never going down) so he could never climb out.
Post bankruptcy he really has zero excuse. He is just blowing his money. I'd like to see him really destitute. If this is how panicky he gets when he is still dropping a couple grand a month on gacha and still has money for door dash and total wine...how would he react when he really is broke and not just crying poor.
Desperation brings out the worse in people and he hasn't ever hit desperate before. It was all manipulation prior to now. Would love to see him actually struggling and what those rants would be like.
We'll find out one of the these days. It may be years from now, but it won't be double digit years, because Phil isn't smart enough to coast the way he could if he understood how his bread is buttered, and lacked any psychological obstacles to exploiting it to perfection. And has already lost enough support that, if things continue like that, the projection isn't good.
As for what I think it will look like... It's hard to say because you are right about it being an unprecedented situation, that he is not prepared for, but I expect that Phil will be in denial about what it means for his future, because he's that type of person. For a lot of reasons, he will not see that his tips being barely above $0 every stream is an indication that he's sinking in a whole new way, he will only concern himself with the way it affects his Champions spending. We're not dealing with a mastermind who knows what he's doing. If we were, he would be playing gacha and have a savings, at the very least. There's no such thing as anyone having the last laugh when their destiny is to die an old person who still needs to stream six days a week just so they have any money at all. I don't care what Phil brings in on his final stream, he loses if it's all the money he has. He himself thinks so, and well know it because look how miserable he is.
When single digit intake streams are the norm, he will ramp up the guilt-tripping and bitching. When that gives way to no tips or Superchats, ever, he'll probably just straight up snap because his addiction is killing him. Phil will not see, or accept, that the good times are over until he's being evicted from the Wakhando and having to come up with a lie to tell his parents about why he needs to come home "for a little while". And even then, he won't grasp or admit as to why everything fell apart after all those years of surviving having the worst rep ever.