if the irs notices this and gets pissed, it absolutely puts his 'helpers' in harm's way. by continuing to not file taxes, the probability of irs aggression only increases with each passing day.
i'm all for giving people a 2nd chance, but he still hasn't realized that it's his fault, and only his fault.
It does not appear that he is purposely evading taxes. I agree that it is his fault that the IRS is pursuing him, on the other hand it seems pointless for the IRS to pursue someone with so little material wealth.
[1]: http://www.irs.gov/Individuals/Do-You-Need-to-File-a-Federal...
I'm not sure how to resolve that.
What doesn't make sense to me is that if he's as poor as he claims, he may actually qualify for a lot of assistance in the form of earned income tax credit, food stamps, section 8 housing eligibility, etc.
I'm not qualified to judge his past behavior or what not but by looking at his bank statement, he doesn't seem to be spending his money wisely. I live a few blocks from him so I recognize those places. Rotten Robbies is a gas station which usually means overpriced groceries and sundries.
If he has the ability to work, he could invest the rest of his money into renting a car and then driving for Uber or Lyft. Uber is guaranteeing $40+ per hour for 6 months which is a hell of a lot more than you make as a dishwasher. The only consideration is if he can keep a 4.9+ rating out of 5.0 which seems like a stretch from someone who may be having problems.
I'm not sure that's actually true. Is it? If you donate money[1] or buy something from him, you're giving him property; whether he is properly reporting that property and paying any necessary tax on that is his issue -- he's not asking you to enter into a conspiracy to hide anything.
At the very least, he could use cash donations to pay off whatever lien is against him. And according to [1] below, the recipient of the donation isn't the one paying taxes on the donation amount.
[1] The gift tax doesn't apply for amounts under $14k or so per year, according to Wikipedia: http://en.wikipedia.org/wiki/Gift_tax_in_the_United_States