Original plan was to turn it into two units as it has and upstairs and downstairs entrance as well as a master bedroom upstairs and downstairs.

It was installed in a house that is over 100 years old and the subfloor wasn't perfectly level, but not horrible.I'm seeing seems open up near the bottom of the stairs/entrance and in living room area, I guess mainly the higher traffic areas. 

Consider separate entrances, utilities split, and winter leasing strategies.

It is zoned for SR7, a single-family home, but is being sold as a multifamily home since the property was converted into 2- two entrances, 2bed/1bath per unit, separately metered electric.

Needs new flooring indoors in all areas (4 bedrooms, entrance way, hallways, 2 bathrooms and kitchen, 2 new windows, and 3 stand alone ac units for kitchen) Needs kitchen remodel, 1 possible new bathroom remodel.

That 6 ft privacy fence is a good start, but you could also include separate entrances, designated parking spaces, and clear instructions about shared spaces (if any).Noise Policies: Include quiet hours in the STR house rules (e.g., after 10 PM).

.), the location, depth, and capacity of utilities to service the site - including public utilities (sanitary, storm and water services), franchised utilities (power, gas, cable), capacity of the local streets to accommodate additional traffic from your development...Be sure to find out if there are any specific local ordinances you need to satisfy (possible tree & wetland surveys, together with any necessary tree & landscape or wetland mitigation plans) and whether there are any concerns from municipal departments (e.g. hydrant locations from the fire department, storm inlet and retention requirements, as well as asphalt / concrete road requirements from the engineer), entrance requirements from the road commission (left turn and passing lanes at the site entrance), etc.Once you get past all this you can finally prepare a preliminary site plan and enter the political arena to get preliminary site plan approval, and to address any concessions the board and neighbors want from you to overcome their objections to your development.

Another option to consider is using the space for Airbnb or mid-term rentals.Here in Texas, basements aren't common, but I found a home where the third bedroom had its own entrance right off the driveway.

We have 1 bedroom, bath, kitchen, living, and walkout private entrance.

Likely, the entrance barrier is not that high but the leaning curve is pretty steep.