Definitely doable though.

In a a maximum over-funded policy design, that gets turned around so that every dollar of cash value is purchasing a legally-defined minimum amount of additional death benefit protection.

I will definitely send Letters, Postcards, Call, and Text, but how often?

I think this is where I would get the most value and it definitely has the most opportunity but again, as foreign as a flip phone. 

I am currently using AppFolio at my current job as a CFO so it is definitely robust.I've used MRI for a short period of time so I can't say much.

We've been purchasing from land flippers, so some of those wouldn't be concerns for these particular transactions, but definitely as we move up in the note investing world and start purchasing notes for actual houses, all that makes sense.

Insurance, proper legal protections, etc. 

What are the best practices for legally converting a portion of a home into a duplex?

The Water Department still asks for the affidavit because they don't consider 'equitable title' ownership unless it's 'legal title'.....so I'm wondering if I can specify timely payments of the water bill in the LC as part of the performance of the contract (or would you recommend I put the water bill in my name on a Land Contract situation too?)

Should I seek legal counsel to ensure this is all coordinated through someone I trust?