One of the things I learned in my Psychology undergraduate degree program is that incarceration is the BEST way to get an offender to repeat. I also know from experience. My middle son had a rough time growing up and did some stuff. It bought him a very short visit to the city jail. In his time there, here's what he learned, how to be a bigger, stronger, better criminal. it was essentially Crime University. Add that to the fact, as you noted, that many longer term inmates have been inside for much of their adult life and have no idea how to cope on the outside. They become institutionalized. While they may long to be free, there's comfort in the system they know and as they say, you dance with the devil you know.
And as someone who knows the system and is, well, honestly, very jaded, there's precious little in the way of actual help. I wonder why that is? Could it be that without recidivism many prisons would close and people would loose thier jobs? COuld keeping the system prooped up have anything to do with it? I know you and I (and your wife) have touched on this before, but aside from a handful of workers I've met, there's very little in the way of incentive to actually help these men and women, many of whom could live productive successful lives on the outside if given the tools.