I beg to differ. Here are the economics of going to jail voluntarily vs. staying homeless:
1. Jail = free food and drinks. Homeless you have to beg for every meals.
2. Jail = free shelter with air condition. Homeless you have to sleep under the bridge.
3. Jail = free education. You can study to become a lawyer or doctor. Homeless - no library to study.
4. Jail = free mining (not with s5 but with a usb miner) . Homeless- you are being mined by jerks
There are so many advantages for being in jail vs. being homeless.
Careful, not everybody lives in US and there are countries where jail offers .. very bad conditions. Most of the points of your "nice" list may not be available.
Also, I am not convinced that you'd be allowed to carry such personal items in a jail, like a miner, even USB miner. Where would you connect it anyway, you'll get your laptop too? LOL! Is that jail connected to the internet?!
So yeah, I'd say that your question was not well enough thought on. And no, I am not stupid enough to waste my life for a few coins.
I know that the daily job is the modern slavery, I know that some think of it as prison, but I have some free time with my family and the job can pay for more coins than I'd get by mining, really...