James - I arranged financing this year for properties occupied by a Valvoline franchisee and Caliber Collision and have a Jiffy Lube property currently in loan application. 

You can make the business arrangement how you like, but you go the relationship more openly.  

I've found that it's not difficult to do at all as long as you set up the proper arrangements beforehand.

Ideally, this arrangement would assure us of an answer in a reasonable amount of time. 

If tenancy is to be continued beyond this term, parties should make arrangements in advance of the expiration.And then in the additional terms:TENANT'S NOTICE TO VACATE: Tenant must provide Landlord with at least a thirty (30) day notice prior to ending a month to month tenancy and vacating the unit unless a longer notice period has been set forth in this Agreement or in an addendum.

I assume you have a clause in your lease agreement that describes this arrangement? 

As of right now I have nothing planned, providing my unknown availability (funeral arrangements pending).

When my wife ran our Airbnb, she spent about 5 hours per week arranging cleaner, answering messages, dealing with reviews, repricing vacancies, etc.  

Can this insurance arrangement leave a back door for popping the LLC protection bubble if worse case scenarios occur and we get sued?

Does anyone know of an insurance company that would insure such an arrangement?