It's all bullshit.
He's not having any more significant troubles than he's had in the past week/month/year. His life doesn't change at all. If he had his way it'd be a completely flat trajectory from where he is now until he dies. He's likely had to shift his spending habits more toward Kat or bills and that has him all ass-chapped about losing all that fun money so he's turned the dial up on the begging and now he's "stressed". I guarantee you it's because he's got his eye on something shiny and expensive and he can't afford it yet without dipping into the red and getting bitchy phone calls again. He's got just enough impulse control not to jeopardize anything but not nearly enough to keep himself from putting the pressure on his pigs so he can buy whatever it is he wants.
Interesting theory. I myself believe that he has a delusion or perceived target of how much he thinks he's supposed to make. I think the money he was making during his golden age with project 7, and all his friends, before the adpocalypse, and compared to his current state, feels like he's about to fall off a cliff financially unless he can recover.