Because I run a business and Uncle Sam is up my tail-pipe with a microscpe BUT also because the state and commerce dept/ require great records to assure our client's are being fairly treated and legally served.

I worked really close with my insurance broker this year to make sure all of our properties were properly insured too because of rate increases and he assured me that my primary covers it and it’s listed on my primary and it’s also listed on the separate umbrella policy.  

Restrict to secondary family rooms etc.At least you can keep things narrowed down to assure less wear and tear on the whole place.

These might sound like standard Mortgage Broker qualities, but I can assure you they are not. 

But, also to avoid markups and assure payment for lien purposes.But, when a contractor gets discounts prepayment may not be avoided. 

My understanding is that most cities regulate the residential assisted living space.Have you checked to assure that you can get a license for the property? 

If it works well enough doing that, then you can buy it, Airbnb it and rest assured that if Big Brother cracks down, you've got a viable Plan B.Also, I'd definitely contact zoning/planning in your area.

Farmer Insurance agent assured me that the rental property is covered from tenant and/or vandalism damages.

Even if you use a 3rd party GC I can assure you quite a bit of your time will be taken up overseeing their work.  

Fico is only a story of the past, it does not assure any certain future.