Your son sounds like my own who is 29 almost 30. With us, there has been no incarceration but all of the other stuff is there: impulsivity, not learning from mistakes, dependency, making others responsible, drama, etc.
I have come to the point that I cannot have contact with him, for the reasons you cite. He gets frantic when he has gotten himself cornered, when there is no money, when he has nowhere to live. And he feels justified in making these our problems. Either hitting us up for loans that are never repaid, or squatting on our property, or not wanting to pay rent, or taking our food.
His own poor choices got him in each of these fixes, and he feels justified in making it our problem, when his choices result in the problems that anybody except him could have foretold.
From my own experience, I do not believe your son will listen to rational arguments about how he got into this mess, or how he can get out. He will not see his piece. More than this, he will not be able to tolerate the anxiety and stress that he would feel in the process of developing a pragmatic and reasonable plan, and executing it. What he wants is that YOU MAKE THE PROBLEM GO AWAY, by making it your own.
He is desperate and he wants out of the predicament. Just like an animal gnaws his own leg to get out of the trap. His job in relation to you is to make you feel the pain that comes from his gnawing at his leg. And to feel responsible for making it stop.
There is no way that interaction with them when they are in their traps will yield anything but pain and their transferring their own desperation to us. They not only want to make us responsible, they want to put their feelings into us. Because to make us feel desperate, is to manipulate us to act in their behalf. It is also to momentarily to alleviate their distress, by locating it in us.
You are in a tough spot. As long as you do not comply with 100 percent of what he wants, when he wants it, you will be his target.
Which is to say based upon my own experience, as long as you speak to him, he will target you, if you do not fulfill his requests.
Your only options as I see them are to limit contact with him, either to a specific time interval each week, when you can be better defended and prepared. Or to tell him you will correspond by mail.
There is learning here for us:
They are responsible for their lives,for their errors, and their compounding their errors, ad infinitum.
Learning to sit tight, even as we watch the train wreck, is our learning.
Our boundaries are our responsibility. The expectation they should take responsibility while reasonable in every other circumstance, is unrealistic here. They will not, as long as we are taking responsibility for them. In my own family, I saw that my very presence, be it by phone, or in person, precluded my son's taking responsibility for anything. There was no boundary that he respected. He violated every single one. I had to remove myself completely. It is a nightmare for me. For me, it ceased to be for his welfare, that I set a limit. That was the difference, this time. I set the boundary for me. To survive.
I am wondering if you are describing such a situation. That the consequences to you, are so noxious, of engaging in conversation with your son, as he suffers, is unbearable. As I type this I am wondering if there are techniques you can use to stay present, while detached. Like meditation. Or some parents just listen and comment, like, I see. Or deflect any question with responses like "I know you can handle that" or "what is your plan?"
This is all very, very hard. I have been at this site over three years, and I am only now beginning to get this, and beginning to put this into practice. Your circumstances will help you. Because you have not much choice.
I know a mother whose son was arrested for 3 strikes. This means there is a mandatory 25 to life sentence. The crimes this man committed were really relatively minor. There was nothing violent about him. He was a drug addict. This is when the mother finally drew the line. Over and over again before she had helped him. She did not do so, this time. The son is in prison for life.
The thing is this. Even when there are the means to pay the bond, or even forfeit the entire sum, should he abscond, we do not know where this will end. We hope and pray this will be the worse, and that they will wake up, and go in the other direction.
But maybe it is the reverse. Maybe they need this lesson, so as to stop now. Maybe the wrong lesson is to help them out of the trap. Maybe they need to feel the pain of their own choices. Maybe gnawing of their leg is not the worst thing. Maybe it is their life at stake. We do not know.
There is not one thing easy about this. But I wrote on another thread today something I need to remember: courage is the other side of love.