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Need money saved up? Naw, though having a bit of boot money under your insole can ameliorate bad situations you might find yourself in. Work can be found just about anyplace, as there is always something that needs to be painted, or repaired, or moved.
Begging is too easy & I've seen too many folks fall into that mindset of it being THE way to put some coin in the pocket. But let's say, for sake of argument, you pull 50 bucks a day, on average, starting out. Five years later, you've made subtle adjustments to your approach & now pull a hundred or better, on the regular. Who gives a shit? Improving your begging game over time is not much of an accomplishment. That being said, I still usually try to kickdown if I got it like that.
Freedom to move around as you wish is a wonderful thing, easily the most attractive part of the concept of becoming homeless/homefree. But like any other way of living, it is not without its inherent ups and downs, and the downs tend to be of a nature that requires one to be made of sterner stuff.