My primary concern with two separate leases is that it would be extremely challenging for you to remove a tenant via eviction for any reason because technically it is one unit.My recommendation is to provide one master leases signed by both groups of occupants.

From what you said it sounds like a short term rental could be a good move, and the tax benefits could be significant if you look into the short term rental tax loophole. 

I would love yo help identify how I may be able to help you.

I expect that I'll be reserving time in various resorts and farming those weeks out to perspective vacationers, does anyone know if VRBO, or AirBnB, or some other site would be most appropriate for this approach?

It checks all the boxes to be legal - 2 egresses, windows, 7' ceilings, bathroom, full kitchen, etc. 

Would be 6 to a building, 30x120. 

@Julian FrazierWelcome to the community and be ready for a huge amount of information at your finger tips.

I’m an OOS investor and I’m sending my realtor over to inspect these properties to see if either one would be a solid addition to my portfolio.

@Max Servais if this will be your primary residence, you will need to insure this with a Homeowners policy. 

Was wondering if I could turn one of my spaces into an assisted living multi-tenant facility as it’s in a great area for it and can be changed with a reasonable rehab.