I think that you are trying to answer a lot of questions right now that you don't have to. I think that you should take one day at a time and worry about you and the baby today. What happens tomorrow will happen if you want it to or not. You don't have to worry "when" he gets out, as it is really none of your business.
I know he's the baby Daddy, but I think any judge knowing his history would not send an infant to spend time with him, unsupervised. Take some deep breaths, stop worrying (if you can) and only make decision that you need to make today.
Don't force a solution, if you don't have too.