Vaya
I'm not judging you *at all*. I just share what my late husband and I did. My sharing that with you in no way obligates you to do the same and it is not pressuring you to do the same, either.
You have to do what you think is best, what your heart and head are telling you to do.
The following I share just as a point of information. The last time that my stepson was in the hospital and my husband was still living, we went to see him (he was in another state). He was released from the hospital to rehab arranged by the hospital's social worker. From here, he went to a sober-living house in yet another state and got a job. Slowly but surely, my stepson made the decision to drink again and left the sober-living house. He gave us some song-and-dance reason for it, but we knew.
At that point, the only thing my husband was willing to do was help him pay for drug and alcohol treatment, and that he would have to make the arrangements himself if that is what he wanted. Beyond that, my husband was not going to help anymore with rent, phone, car, nothing. When this happened, my stepson was 31 years old.
He has been homeless several times in the past. Been in county jails and in prison. Walked or biked wherever he needed to go. He always eventually ended up on someone's couch or rooming with someone. Amazingly resourceful he is...
Now, he lives in another state, and I haven't spoken with him in many months. He somehow manages to get by, although I doubt I would enjoy hearing the details. He will never be invited to live with me now that I am alone. I simply don't trust him especially now that he has added Heroin to the mix. I deserve to feel safe and at peace in my own home. And that is what my house is, my peaceful home.
As I said before, when it comes to your son and your house, you need to make decisions that you can live with. Because you have mentioned that your current 'agreement' seems to be loosening--meaning he is not being compliant with the original timeline? Is that right? You asked whether or not that meant he was "playing" you. Well, I can't tell you that, but when similar things happened with my stepson, yes, we were being played (or at least he was trying anyway). We decided that whenever he did not keep his end of the bargain, we were free to not keep up our end (pay for the phone, help with a deposit on an apartment, and so on).
vaya, you have to decide what is best for you. If that is keeping your son with you, then that is keeping your son with you. You have every right to make that decision. You are closest to that situation--not us. I wish you peace!