I have about a month and a half to get the place live, not doing any renovations beyond painting....1.

In order to set up what you are trying to do properly, you need an attorney AND a CPA who agree on strategy and structure so things work in tandem. 

For operating risk, a common starting point is three to six months of fixed expenses at the property level—property taxes, insurance, utilities you’re responsible for, management, and a prudent maintenance buffer.

Very close to Greensboro, and has a very established MTR market due to demand made by hospital and a corporate travel (Hanes, RJ Reynolds). 

In contrast, rebuilding a garage is a time-consuming, on-site process that offers more customization and durability but incurs higher costs and a longer timeline due to foundation work, on-site construction, and permitting.

Does anyone have a ballpark estimate of the cost to build a new side-by-side duplex in duplex which is 3–4 bedrooms, 2 baths per side with each side being approximately 1,500 square feet per side with a 1 car garage and a basement?

A delay in the contractors and a slow market pushed projects into that red zone where you need more time and it comes at a big expense. 

Fewer tenant “too hot/too cold” calls and a nicer look overall.

After all, he also was in real estate AND a successful baseball player. 

There has been talk ongoing about regulations and a moratorium on STRs there so I would call the city and see where they are.