I’ve been reading a lot about business books, negotiation books and I seemed to had an analysis paralysis because I felt very stuck even though I am learning and preparing.

Might help drive some business toward you but also show the municipality that you are taking an active role to help non clients make their STRs better for neighbors.

Maybe if there were a crime spree terrorizing the entire county, but I'm not even sure about that.The bottom line, in business and in government is, "where is the money going to come from?"

The LLC is the business structure most use when investing in STRs.If you're extra worried about liability you could split the 3 properties into 3 LLCs but to me this seems like a situation of "If it ain't broke don't fix it"

I'm sure it is in everyone's best interest to be doing business with as much knowledge as possible.Setup a phone call with them, I'm sure they will be more than happy to talk with you.

These are all solvable problems you can draft a business plan for, then propose your strategy and projected business benefits to the host.  

Have you reached out to friends, local groups, businesses, schools, hospitals, etc. telling them about your rental and the special promotion you are offering to their members?

I can speak to two of the ME mountains - I prefer the areas around Sugarloaf and Saddleback mountains since you also have the lakes there (Rangeley Lake and Flagstaff Lake) which drive more consistent business in the summer months as well.

They care about the occupancy and financials a lot. 4. if you are going to run a owner occupied business out of the property such as adult care facility and you are considered 51% owner occupied you can do 20% down and really good rates. 

Hey Gregory - we do a lot of business with the rent by the room model in South Atlanta (College Park, Riverdale, Jonesboro).