The thing that concerns me is that boyfriend doesn't have a job, obviously, if he is ready to do jail time because he thinks it'll be cheaper than community corrections. He's probably right, given he has all this free time. Those programs, especially the ankle bracelet things are pretty expensive most of the time because they are done by private contracting agencies. But that he's not bothered, in eleven years, to take the steps necessary to get his license reinstated is quite telling. It is costly, and requires proof of insurance, and jumping through several hoops, and he's elected to just not deal with it, taking the gamble he'd never be caught. Knowing this about him, I'd guess he's probably pretty familiar with the whole scene, knows he can do the time and isn't overly worried about the middle class preconceptions some of us have about jail time.
Incidentally, I agree wholeheartedly with everything that tranquility says about joking about anal rape in corrections facilities. It's not funny, and people who are incarcerated do not "deserve" this sort of punishment as part of their sentence. Not long ago, there was a broken windowpane in a correctional building on the public road near here. Several people wrote letters and called the local tv stations asking why the county didn't fix the broken windowpane. Then there were some people who said, "Why should they fix it? Let those beasts suffer with the cold! They don't DESERVE a warm facility!" Idiotic, of course, because the cost of having the damaged window repaired was much less than the cost of utilities and the idea that the inmates should suffer and have to endure inhumane and abusive treatment from each other and the guards should have gone out of fashion years ago, along with torture and public hanging.