Something else is a factor here.

My main focus is really to reduce the number of closings (due to fees) and to pay the family member back for helping cover some previous work.

Some restaurants will let you bring a bottle of wine , but charge you a corkage fee. 

What their top dollar is depends on a lot of factors and whether or not the bank pays the back taxes before the sale or after doesn't really matter. 

I had already factored in self management...I’m just wondering how people do just continuing STR over the winter months.

Remember in North Carolina there is a (considerable) diligence fees with any offer you make.

I've seen it done two ways:Flat rate lease - The operator signs a lease for a flat rate and runs the business collecting their rent and care fees from the residents. 

NO reputable lender asks for funds upfront besides appraisal fee.Have heard MANY horror stories related to upfront fee lenders and it rarely ends well.

Population growth and job growth are key factors.

I would venture to say that 95% of properties listed today on the market will not cash-flow at a 7-8% investment interest rate once you factor in principle, interest, taxes, insurance, and a maintenance / capex reserve.