In my humble opinion only, this sort of sounds like "rinse / repeat" ... by taking calls / answering texts so frequently and engaging in questions, detailed discourse, showing concern etc., you show and validate that you are still there for him / for his needs and wants, even if just to contact, to feel another presence in his desperation and doubt as to what he is going to do, to think you may be someone (again) who may (you already did) give in and rescue, as has happened before again and again, and which he no doubt believes will happen in a crunch. Sorry Lil, but it looks like you really do not want to detach, you want to keep the strings attached, keep connected, and he does not want to really let go and really does not want to be on his own either. I think he can sense your concern, your fear that he can't make it, and he in turn internalizes it also.
Of course he wants an adventure (why not?!) and wants to try, but he does not seem like one with the capable, adventurous, confident, outgoing temperament, and skills and knowledge to make it happen easily. (Maybe I’m wrong.) To pull up stakes and make a new life, to me it would take a real motivated, ambitious, efficient, go-getter person to make it happen the way he was thinking it would. (I don't think I could do it myself.) From your posts, I don’t really get that’s how he is. (?) What if he is not successful there? Do you really think this is the last time for you to fork over $$? Will he call you again for more $ tomorrow? Or eventually for a return train ticket? Will he return back to you?
To me, he seems still soooo young yet. And I do understand your reluctance to let go, especially when he seems so needy for a connection with you. I do know the love, I do know the fear. What experience does he have in a strange place to make a new life? You are right in recognizing that there was no planning or forethought. So what likelihood of success? What did he do before / where did he go when he was previously out of your house? I think "nothing is going to change now, if nothing changes" (that is repeated over and over on this site). Things here with you and son seem to be continuing on the same old road … If you continue to take his calls and answer his texts and bail him out, and need to know everything, what has changed? Are you detaching? Is he?
If the intent for his going to CO was to throw him into the “pool” and let him “sink or swim,” it doesn’t look like that’s what’s happening. It looks to me like a slim tether (life saving) rope keeps getting thrown out to help him stay afloat to keep trying to make it. And maybe he will make it, and then again, maybe he will need to be rescued, if you cannot bear to see him go under for long enough to feel the desperation to want to fight himself to find a way to survive himself.
Why should he feel desperate to find a way on his own, if you rescue him over and over? He does not need to find a way – you find it for him - you make the way for him. And now you said “This is the last time!” ~ Do you believe that? I don’t think he believes it. (Actions speak louder than words. You have not previously shown it in your actions, and until you do, it is empty words.)
From my own experience with others of my children (not my Difficult Child), you might consider that your additional financing for him to get him set up there (nothing more fancy than a cheap single bedroom / shared bath in a boarding house) for a month or so, to put him in a place where he could then be of a mindset to think about getting work and not thinking about how to sleep and eat safely. I only suggest this because you definitely do not want him returning home to you ~ and do not want him returning to J. And that “set up” could definitely be that last time, if you stick with it.
I know these words probably sound hard, but these are things I am telling my own self also about my own difficult son, who is much older. (Others also told me similar things in a blunt way! I needed to hear it!) This is just how I’m seeing the picture from your posts. I’m learning here along with everyone else.
Know that I am holding your heartache also, Lil, and do believe there is a way that we are going to be alright. Take care, dear.