The title company itself has lawyers and people who make sure you are covered in the legal aspects.

Are they soliciting feedback from showings to understand why people are not interested?

I lend money privately and would never consider this as it is dependent on things out of my control (permits, neighbors, you being a good host, rental demand etc) I sell a ton of STR that are in actual resort communities and have great amenities and they are all  competing for the same guests, I can't imagine that there is a need/demand for this type of unit.

Life is too short to have to put up with these kinds of people in this business, even though this may cause you a short-term interruption in revenue. 

Any one meeting people on here and partnering up to make it happen !

Are you talking about permanent movers, or those on vacations of some sort, or people who are temporarily to be housed due to an emergency and then intend to move back to their old stomping grounds?

He imagines just us and our family.

While starting off with this strategy you could also be studying more about value-add options and start attending meetups in your area to get an idea of what other people are doing. 

In the past I have seen the FDIC telling people they will not be able to touch their money for 20 years in such instances.

I think people think of daily and even weekly rentals as truly transient renters, whereas monthly and annual rentals as being more resident based.That said I have seen 14 day minimums and 3 month minimums as well so while by and large monthly and annual terms are common they are not all inclusive.