Is it possible that Phil actually just wants people to be nice to him? It's pretty clear that he's starting to break, and he's said several times now that he doesn't have any friends. He might just be desperate enough where he's painting himself as a victim to get pity points from his audience. It also has the added benefit of bringing in more donations too. I really think it's more of an attention thing, he's egging it on further by saying shit like "nobody has actually guessed it yet, but I'm still not going to tell you even though I am acknowledging that I'm aware you're all talking about it."
Usually with Phil, the vaguer he is about something, the more full of shit he is. Phil has shown in the past that he has no problem openly discussing his problems, like with Machinama. If he was being audited by the IRS, he'd be kicking and screaming about it and talking about bugged tax laws or something. Something with the condo association seems a little more likely, and I could see him not naming them specifically because he doesn't know how to spin it yet into it being their fault and not his. But even then, I feel like he'd be complaining about their policies being unclear, or him being too busy to adhere to them or whatever.
The "not a business" claims are a little weird, but I think he might just be trying to paint himself as the underdog. He's not a business, he's just an innocent gout ridden dood trying to make it in the world, but all these detractors keep getting in the way of his self employment. Basically, he's trying to humanize himself.