I am actually wondering if, let's say DSP were to win a million-dollar lottery, he would stop begging. When you listen to the script he has been repeating for literally years now, i.e. "I am currently in the worst situation I have ever been in", "I need your help so if you can, please contribute", "I'm overdrawn" and all that, I'm wondering if he would stop considering the begging is so ingrained into him. It seems to be part of who he is now. Without it, he'd have nothing to talk about. His financial situation is pretty much the only 'interesting' thing going on in his life, and without the good old 'oh woe is me', he'd just be a scumbag human being, period. Now he has the excuse of 'Trolls fucked me over, if they hadn't put me in this financial position, I'd be the coolest dude ever, but now I can't because STRESS AND TROLLING!'.
I'm starting to believe that Phil would be a beggar no matter what, because if he wouldn't have to beg, he'd have to realize his nature and personality without negative external factors is still rotten to the very core. His begging gives him that delusion of "it's not my fault I'm a worthless sac of shit, it's because of my financial situation!".
I think an argument will be that if he were to win big somehow, he'd live as a true hermit watching WWE everyday while downing gin and getting even fatter on his shitty italian sauce, but I'm not so sure to be honest.