But is that controlling on my part? Or just the expression of an opinion?
Nope not controlling at all. There is no reason in the world for you to do all this for him. If he really wants this 'type' of job, well gee, I guess he's going to have to 'earn' the money at another type of job first, one that doesn't require all this 'up front' pay out. That is being an adult and handling things in an adult manner.
I am surprised that the sober living facility would even approve of such a 'vague' job. When I was in the Recovery House, we had to have a job with 'set hours.' No travelling all over hell and gone and back. We had to leave our daily or weekly schedule with the 'House Parent' and phone numbers where we could be reached. Not that they ever called me, but I think it was a way of earning their trust.
Now, if I were you, I would say NO at this time. You don't have to give a reason. NO is a complete sentence.
J M H O
Love and hugs,