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

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.

We make people take photos of themselves holding their ID and then I also meet them in person for the showing - at least for my units on the NW side of Chicago.I've never heard of these testers, but I am not surprised. 

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. 

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

Jason Chambers is the guy I refer people to.

I also wouldn't touch hilltop with a 10' pole. struggled. old homes, over budget renovations, lots of issues. realtors push people here since it's the only place cheap houses close to downtown can be good but homes are 1900-1920.

I usually like to start it shorter to be safe if I need to end the tenancy, but I know some people opt for the longer 14-15 month leases.

The real estate landscape is always evolving, presenting new opportunities to discover.