The best practice is to provide guidance early and often. 

But if I want to invest money providing better terms than those options, he's happy to take the better terms.I don't want to ask for the terms of his best alternative, and even if I did, I'd likely still post this to verify.

The rate will be high but you won't have to provide any income documentation or leases. 

Does anyone know of reputable insurance providers they recommend?

Did you ask what about the inspection caused their last deal to fall through and whether they have a copy of the inspection they could provide to you?

Consider semi-furnishing the space to increase room rental costs and also contact your local university/college housing department, they typically provide students with resources for off-campus housing and you could plug yourself in there. 

The landlords didnt provide walls painted with marks or drawings on it. 

- 3 units are occupied by seller’s close family - All units are on month to month basis- All units are significantly under market rent- 1 unit pays on the 15th of the month- 1 unit has not yet paid for Match 1st even though my information has been provided to them twice- I have no applications or old leases1.

TLOxp: TLOxp is a comprehensive data platform that provides access to a wide range of information, including property records, criminal records, and more.

Look for better deals to provide latitude to deal with unforeseen issues.