I had a similar problem with somebody I was supporting, they always made promises that they would pay back, get things straight, etc. It never happened.
What I learned from the experience is that ultimately you have to trust people's actions above words, and be very firm about deadlines. Otherwise there are definitely folks who will stretch any situation where you give too much leeway --not that I'm accusing anyone of doing that here, but that it's just a thing to watch out for.
Personally, my biggest worry is that if somebody is causing drama, that if should they not get their way on some occasion, they might escalate said drama to the city or local regulatory bodies. I have seen this happen with the community in San Francisco and the result was not good.