I don't feel bad for him at all, honestly. I feel bad for the people he hurt along the way and treated like assets, but that's another story. I don't care about his dents, but it's how he treated John, Howard, and Respect the Pack towards the end.
Phil is someone that got everything he wanted in life and he always wants more. He always wants more money, more six star Hogans, more dents to hand over their SSI/SSDI checks, more money for taxes from his (NOT) dying parents, etc...Phil has had EVERY single hint of adversity removed from his life and has YET to experience any form of hardship.
If Phil was even a HINT of a likable person, which he's not, I would feel bad. There are people out there that have shit luck, but are at least likeable people and don't let the bad times get them down too bad, but not Philly Warbucks. His entitlement and negative attitude towards everything in life, that he thinks he's God's gift to the world, but when someone tries to disagree with what he has to say, he gets butt-hurt and holds a grudge against you...and he waits until you experience some hardship, that's when he comes back and laughs at your pain. He laughed at Machinima went under and everyone was fired from there, he laughed when his old boss was fired when the helicopter company was bought out by Sikorsky
This is the same dude that has held a 20+ year grudge against the Cannon brothers because they called him out on his bullshit, hell he still does to this very day. He rants about rollback netcode every change he gets. Like, dude. I'm sure the Cannon brothers don't lay awake at night cheering each other on for telling you to shut the hell up when they were in talks with Capcom, but I'm willing to bet a six star Hogan Phil does, as he sits on his phone wishing nothing but ill will towards them.
Point being, I don't feel sorry for him at all. Phil has gotten everything he wants: to be alone in his mid-unit condo that's falling apart, no friends, no immediate family, no nothing.