This has always been my assessment of his so-called money troubles. Ever since the divorce, a big part of Boogie's self-image that he wants to project to the world is that he is a smooth-talking gigachad that gets more HAMS than a butcher's shop window. All of his sugar babies are actually his real girlfriends until it all falls apart, then they are retconned as, for example, 'some stripper'. Hiring these whores on a long-term basis has never been about the HAMS or companionship in my view; they're props to perpetuate his image as a ladies' man who can endlessly talk this stream of barely legal girls into his bed using his charm and being a nice guy uwu.
It seems his goal is always to slowly turn off the flow of cash and gifts to these girls, and use his relentless woe-is-me pity baiting to try to manipulate them into being the live-in maid that he's been desperately chasing since his wife left him. As much has been said by some of his previous victims. I will leave open the small probability that perhaps he finally found one that is so zonked-out and low IQ that he managed to make that dream a reality. I'm nearly certain that by far his biggest monthly expense is keeping Megamind around(which he would never admit for obvious reasons), and that's what the vast majority of his recent money-grubbing has been about. As far as I remember she started showing up shortly after his boxing match windfall, and I think that says it all.
Wings felted him on the ring and live! Wings W 
