Some counties in Indiana would refer to this as an Accessory Dwelling Unit. 

You would have to line up carriers that accept LLCs on non-owner-occupied dwelling coverage.

It covers a basic human need (shelter).

These I think are considered rookie mistakes, but I'm all about finding ways to reduce risks from human error.Has anyone else considered technological solutions to help the due diligence process?

Then since your out of control your subject to human nature.

That's human nature.

They become gurus as soon as humanly possible, and their income comes from preying off of newbies by convincing them that they buy, sell, and hold real estate when really they're just selling courses. 

Bc entropy sets in and as humans we all have a tendency to become lax with time.  

I do have them sync their bank accounts and credit cards to eliminate human error in entering items, and ask them to avoid putting personal expenses on those accounts.

I am dwelling on how to scan future tenants and what to have in my lease agreement and more.