Jim over at Blueprint for Financial Prosperity had an interesting post recently on homelessness and giving money to panhandlers. I find this is always a good subject for discussion in the college town where I live, where you can almost always see panhandlers on our main street. My policy is not to give money directly to panhandlers.
The post referenced a local tv investigation on one panhandler in particular, which "exposed" that she in fact went home to her family in a house each night. I'm not completely sure how I feel about the tv piece, though I was interested to see the reporter estimate the young woman could earn about $26,000 tax-free each year. I did a little checking with the IRS on gift taxes and saw that the reporter was correct: panhandlers don't have to pay any federal income taxes from the "gifts" they receive from strangers, according to my read. While I'm not sure panhandlers focus on the tax benefits of their "jobs," I think they might just take the cake for legally avoided all income taxes.