First of all, you want to do your due diligence to make sure you know what your are getting into and hopefully you can get some sort of assurance from the Town that the two family is legally non-conforming.

I agree that the sphere of influence created by going through the degree process and meeting all sorts of folks related to it could be huge for opening doors that may or may not be missed without it.

The larger strategy for the big income change has sort of been set to the side while I've been in transition.

Another unfortunate situation with a lot of these sorts of tenants is that they are "judgment proof", meaning, even if you were to sue them for damages, they do not make sufficient income or have sufficient assets to collect on your judgment.

Engage with local officers to gather insights about the neighborhood, and don't hesitate to ask them specific questions about the property.When touring, pay attention to tonality, body language, and hidden cues from sellers.

And even if it were stunning newer granite of quartzite, removing installed granite is difficult and usually will crack as it is glued down with some sort of caulk.

What sort of risk mitigation will help you sleep at night the most?

I use this to sort of "sell the area".  

Licensing --- Most reputable lenders regardless of whether they only do private money loans or not will have some sort of licensing 2.

Have someone call, email text showing interest in the lead and see what sort of response you get.