TJP, I only bailed my son once after many sincere, tearful promises from him to follow rules, go to meetings, live with a curfew and work hard on his recovery. He hadn't been out one hour before he was on the hunt for drugs again. It broke my heart.
I'm not saying your son would do that, but I am saying that is often the case, even when they really mean the promises when they make them.
I don't know if his jail offers medical treatment, but if it does this is something he could look into.
It's your life, TJP, and if doing something helps you, then do it...knowing the risks and with no expectations. There is no way any one of us can judge another here on our choices, we just do the best we can and when we know better we do better.
Sending big hugs because no mama should have to watch her child self-destruct.