As much as I think a job would fix most of Phil’s financial problems, all those fucked up tattoos have already made sure that will never happen. I mean, unless Phil finds someone who is just dying to hire an overweight potato with a “clitoral dough” tattoo for everyone to see.
It depends. Unfortunately the jobs that wouldn't care about his appearance or lack of any appropriate skills or work history are the ones he's utterly not cut out for. Phil couldn't hack it at a warehouse job; aside from the fact that he's so weak and lazy as to be a liability, his antisocial personality would also cause problems. He would almost certainly get his ass kicked by the other workers for being such a shit tier human being.
Ironically, in this day and age, I'd almost say he was made to be an op-ed writer or some sort of diversity quota hire for a liberal arts department, except he's not a woman, trans, or "PoC," so the type of people he'd actually want to associate with want nothing to do with him. That and the fact that he's too lazy to even write a few thousand words of SJW word soup a week, and too dumb to even fake understanding the newspeak that he parrots back.
Stick him in a warehouse or something. There are plenty of jobs he could do, but he doesn’t even try.
I'm not so sure. Its not just the tattoos at this point. He's got a terrible personality, he's lazy, he's old, he's physically pretty weak and doughy. Jobs that wouldn't care about shitty tattoos still would require him to physically be able to meet certain bare minimum requirements, and I just don't see Phil being able to do that, not to mention the fact that he'd almost certainly wind up antagonizing his co-workers. Phil is cut out to sort donations at a Good Will, or maybe even be a greeter at Wal-Mart (were it not for his appearance and attitude), maybe even working in fast food (except for his atrocious hygiene, but that's something that could be improved with coaching), but he's not suited for manual labor in the least. Again if he were younger and got some experience and exercise under his belt, maybe, but at this point he's likely a liability. I don't even think he has that tard strength going for him.
Nothing ensures success when asking working people who earn money to give you some of it to support your lifestyle of fagging up twatter all day long and dodging thrown beer bottles from Toren all night long quite as well as calling the people you are begging from 'motherfuckers', Phil!

Stay classy!
What makes you assume any of the people he's begging from actually work for money? Most of them seem to be as broke and unemployed as him, maybe getting money from their parents or something. Few members of the troon community seem to be productive members of society. Hell we know that Phil even "seeds" some of that money himself.