My tenants add their bank account, set it to auto-pay, and it's free for them so they're really happy with it.

Roof, water heater, HVAC, any other mechanical issues depending on the age of the home. 

After the hotel dissolved, a corporation was put in its place, and there was a deed which was set onto the land to restrict any activity/business such as there was prior with the hotel in the early 1900's.The Dilemma:As soon as I put in an application for the Short-term rental permit, members (corporation shareholders) of the area had presented a part of my deed dating back to 1922 which states, "may not be used as a boarding house, or any mercantile or mechanical use".

They may be past the point where they could file a mechanics lien on the property.

(Assume worst case like roof or mechanical systems) Assuming you refi out will you be willing and able bring money to the table?

IF we are quoting an apartment turnover and he does not go in the basement and check the mechanical systems, as well as do a walk around the exterior to check the overall condition of the property, I would have a Sh*t fit. 

The box is too full and it's jammed the mechanisms.

That's really the only mechanism that exists in lending that fits to anything close to what you are describing. 

For just one airbnbs auto messaging and quick replies should get you pretty well automated from a messaging standpoint. 

Too risky if mechanics liens, etc.Think buying a pie at grocery store and selling pieces for desert at restaurant to max out profit with land.