Oddly, I have some information about policies in this area.
My pen pal from Federal prison was transferred to "supervised release", which is not parole but works just like probation does.
Part of being allowed out is that the probation officer has to approve the housing arrangements. For a synthetic, this might include chassis assignment. For my pen pal, it was a bit nerve-wracking since she didn't have any housing options on the outside and had to get approval for homelessness.
It was Illinois, I believe, where many nominally paroled sex offenders stayed behind bars because there was no approved outside housing option.
My pen pal's PO would have had to take time to go see a judge to get her put back in prison and didn't go to the trouble, so she did get out.
Which reminds me of some reasons Dale's actions were so meritorious. If someone gets released from prison to a homeless shelter, you can't get mail at a homeless shelter. You can't get a post office box, because the form to get one requires your home mailing address. Good luck re-integrating into the legal economy under that handicap. By subletting to May, Dale made success more possible for her.