There is an incredible amount of points to consider when weighing the options on something like this and honestly, I don't recommend it to very many people at all ....even seasoned tradesmen and investors.

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

People that get destroyed are ones that are enticed by the low interest rate and assume they can refi after the second year. 

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.  

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

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

Jason Chambers is the guy I refer people to.

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.

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

I would closely monitor your competitions pricing to see what is working for them.Vrbo has built in tools to monitor when people are searching for specific dates.