I would start by identifying your overall real estate objectives, both short-term and long-term.

I explain to them I am not in the business of whimsically kicking people out, because that costs me money (see the lead generation paragraph earlier in my post), and my goal is to find really good people to call my properties home and then take good care of them so they want to stay a long time.

You can market it for sale as "no money down" "no down payment needed" etc, and then explain it to interested people.

Do I explain every conversation I've had with the borrower or is there something specific you look for? 

I'd call someone in the planning side who is looking to get units built and explain how their perspective can kill the entire project resulting in no units...so maybe they can help the discussion on phasing it your way vs. the other way. 

Don't do it.Arbitrage can be a really good strategy, but one that is better paired with experience in the STR game and ownership because then you are more of an asset to the landlord than some newbie fresh out of a TikTok class trying to explain why they should rent you a unit so you can re-rent it for mor.If you are in Boston, you can go an hour in all directions and likely find cashflowing rental opportunities.

Can anyone read the sale history of this property and explain it to me?

Owners may unintentionally (or otherwise) make decisions that violate these laws, putting both themselves and your management company at legal risk.Second, your existing screening process, which prioritizes objectivity by approving the first qualified applicant, is there to maintain consistency, minimize liability, and protect your team’s credibility.

I had explained to him that I want to keep my family safe and ensure we are complying with code.

If you do or had to make an exception, how would you objectively and consistently determine a dependent?