To me is strange for anyone to choose a life where he is absolutely not free, just to get a college degree. Degree or not, having jail time in your resume will have a (extremely?) negative impact.
You don't lose that much freedom in the military. At least, most of the things you would be permitted from doing are things that you wouldn't need/want to do anyway.
But I suppose you could say the same about prison, for some people.
How pervasive is that attitude? I've worked with plenty of people with records. So long it's not something real violent or something lame/morally questionable (robbing an old woman because you're her financial advisor) the only real question I think of is "why were you caught" and if that is strong evidence of anything else. Like, it could indicate a poor understanding of information theory, or badly calibrated risk assessment.
Someone committing a nonviolent crime to get free room and board and college, of explained, sounds rather clever. Most people end up in significant debt for a similar outcome. (And low security prison in the US isn't so bad, about the same level as sharing a 2 star hotel room with a coworker, from what I've seen.)
Don't underestimate the value of a place to sleep, a roof over your head, and a rudimentary education to a large portion of the least fortunate. Having the certainty of those things could easily beat trying to hold on to a terrible job and keep a place to stay with food on the table.