[QUOTE=Don’t Call Me Shirley]
In 10 years as a probation officer I have never known anybody to do exactly what is described in the OP. That would be very difficult to time correctly because it takes 1-3 months after the commission of the crime for the case to work its way through the system. Even if you waived all your rights at the initial hearing and plead guilty, it still probably wouldn’t work.
I regularly have people come on probation that say they don’t want the hassle of probation and would rather just do the time in jail. I’ve never had anyone say, though, that the reason is because of the cold weather, they usually say they don’t want the hassle of counseling and community service and me showing up at their home and work unexpectedly.
I have known people that will arrange to spend one night in jail, if it is going to be really cold they’ll throw a brick at a police car or something so they can spend the night in jail. That’s quite different from arranging to spend the whole winter. The possibility of successfully negotiating all of the legal and timing issues would be pretty remote, even for someone like me that’s worked in the system.
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Right, and dudes? Jail is not “you get cable, 3-square meals a day, warm living arrangements, and all the books and library stuff you can imagine”. Jails are very overcrowded, with sometimes 8 dudes in a cell meant for 2. You may get Cable in a communal area, with one channel, and if you can hear anything you’re lucky. You run a very real risk of being beaten up, shanked, or raped. It’s a hard, cold, dirty, nasty, and dangerous place. The Youth camps and some minimum security workfarms aren’t so bad, but you have to be under 18 to get into one, and in the case of the other, generally commit a white collar crime, no priors and a 1-3 year sentence.
If a dude wanted a warm place to sleep there are shelters. Now about half the hardcore homeless won’t use shelters as they don’t like the rules: there is no drinking, no drugs, no pets, a certain bare minimum standard of cleanliness and usually no smoking. But there are none of those things in jail either (in some of either they still allow smoking). Thus all of the reasons for not going to a shelter apply to not going to jail, and there are even more "rules’ not to like.