This American Life did a podcast (can't find it at the moment) where they followed two guys who decided to become homeless, and beg for money in NYC while trying to write poetry and stories. Each guy easily cleared 60k, as I recall. So it's definitely doable.
In fact, another article I read told about a couple in Portland, Oregon that cleared 50k between the two of the begging.
This American Life source does not appear to check out on 60k while homeless figure:
"Gregory: I was making 60 grand a year, 60 grand, not working hard. If I wanted to push it I could push it to 70. They want you to do over time on Wall Street. Wall Street judges you by your overtime. So yeah, I was raking it in. And I was spending it just as fast on alcohol. I would get up at 8 at night, take a shower, have a pint of Jack Daniel?s on me when I got into my car and drove to work."
Poetry sample:
"A Few of My (cough) Favorite Things"
Waking up achy, And out in the open.
Guard dogs are barking. Before words are spoken.
Wrought iron benches, That causes suff-ring.
These are a few of my favorite things.
Taking a shower, With four dozen others. Moving around,
In a stench that can smother. Finding that you,
Are the source of the stink!
These are a few of my favorite things.
When the bottles dry, And the smokes are gone,
And I'm feeling low
