A legal duplex will have everything separate.  

There's lots of properties for sale in the Smoky mountains so you may also have a larger selection of options to purchase as well.

After some research, the two areas that interest us are Vermont (probably near a ski area, Killington or Stowe) and the Smoky Mountain area. 

I'm wondering if there's a software out there that could connect 2 separate VRBO accounts to resolve this issue.

Hoping to add a mountain cabin (both for investment and to bring our three young daughters to when we can).

Recently I bought a retail center and that deal has been making me think more about if it would be wise to set up a separate management company for all the properties. 

@Keith DowdyI see your name pop up in every Beech Mountain post for the last couple years.

And an actual lot split which was a SFH on .85 acre now turned into two separate lots, with a duplex on each lot.

This is a unique home and it actually has a full kitchen, 2 bed and 1 bath downstairs and I think it might be well suited as a very large vacation rental(entire home) or both floors being rented separately at some point in time.  

I have a separate short term rental insurance policy (insurance agent recommended short term policy over long term since it's ultimately being used as a short term rental) Curious if that is the same as the Airbnb $1M liability insurance or if they have a separate one