The loft is very successful on Airbnb and people love the main house for long term rental.

I never was able to coordinate a consistent quarterly meeting for planning, I never knew who to contact because they have multiple levels of their workers and people were constantly moving in and out of the organization.  

Quote from @Andrew Steffens: There are probably more experienced people on this type strategy who will hopefully chime in. 

Which is not easy for possible for many people (like your husband).Once you really know what to do, the risk level drastically reduces.

Ineffective or Absent Conflict Resolution ProcessEvery successful group of people needs an effective conflict resolution process characterized by:simplicity to understand and remember;quickness to start and complete;a clear vocabulary.My company, Livingsmith uses and recommends the 5-on-5 Process for conflict resolution in co-living homes.2.

Jason Chambers is the guy I refer people to.

I get a lot of applications from out-of-area people, typically moving from another state.

My experience has been that although I outline the requirements for tenancy in my properties, both brokers and PMs still send people who would qualify for most property owners but do not meet my outlined criteria; and then are SHOCKED when I reject them.  

I have a couple of people that this has happened to, and you need to have it in writing and tied to the property to make it work. 

I kind of didn't want to mention that on the listing so that it wouldn't turn people away before they even had a chance to see it in person.