I do own all properties under my personal name (liability is covered through an umbrella policy).

The big picture is this: Airbnb/VRBO/short-term rentals can continue mostly unabated.

I would like to contact a local real estate agent to get some market information on comparable sales, rentals, and the overall market picture.

This is a topic for each investor to cover with prospective management companies before hiring one.I know of at least one management company that recommends the owner pay for the renter's insurance (with the cost folded into the rental rate) and advertise that fact as a marketing matter. 

If you get a written cancellation from the buyer you should be covered.

Maybe i'm misreading but when you rent out their house, the first 670 should go to them to cover the mortgage and then you split the profit? 

Pictures are Zillow are fine. 

Is $100/month/per unit enough to cover costs associated with turnover of a unit?

The APIs are not too tough to use, and I would recommend picking a handful where you'd get the highest value and trying to build out a small MVP that could do those for you.AdWords are also a decent outlet for your existing sites, but I imagine you've looked into that already and maybe even have it covered.

Thank you Kim, We do have that written in the lease and we covered our buts for that reason but I'm honestly afraid that he would become even more irate if we bring that to his attention.