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.

On Mon, Jan 21, 2019, 8:16 PM Yardena Cohen <yardenack@gmail.com wrote:
They're not asking for "free rent forever" - I don't even know where
people are getting that idea. Please read the proposal again - they're
offering to continue paying as much as they're able, up to 50% of
their budget, with the understanding that this would settle any
outstanding debts.

Robb, are you talking about the "Out of the Blue" event which is
specifically mentioned in the email you forwarded, which they say was
a miscommunication which they're willing to move on from?

If we're talking about good faith, the most important aspect IMO is
the ASSUMPTION of good faith. That means when someone tells you what
they can afford, don't accuse them of lying based on snap judgements
about their clothes, or of secretly hiding donations because they're
fiscally sponsored by someone else, or of embezzling money just
because someone else "completed the contract" for an event, or of
"holding back-rent as a carrot gift" when they're clearly just trying
to settle their debts in whatever way possible.
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