@Noah Bacon, does the tool kit include design, pricing, bidding, and management features or just the HD Elite discounts (which for some reason do not kick in for me)?

Examples where this has been done successfully include bed and breakfasts, self storage properties needing 24 hour management presence  with living quarters. 

@Elena Dubinski once I knew about tax liens and had a very basic understanding I took an attorney to breakfast and he cleared up most of my concerns about risks.

Nothing fancy, but coffee and solid breakfast sandwiches. 

@Noah Bacon is aware of this.

Quote from @Noah Bacon: Hey Jacob!

My routine, 1-2 hour breakfast/coffee with my buddy.

@Noah Bacon This link does not work.

Renting by the room is almost like running a Bed & Breakfast or hotel except for longer term stays which is why they often are not allowed in R-1 residential neighborhoods.

This could make your ADR less competitive, but if marketed correctly I'm betting that people might perceive more value, which keeps occupancy at least the same.I'm thinking of a model where you tell guests they have "add-ons included" like grocery delivery, prepared breakfast package, attraction tickets, inner tubes, etc.