Many owners of older hotels faced very low occupancy during the pandemic; so, many of them accepted government ICE contracts. 

Also in terms of collecting rent, would I need a lease agreement, and account for this during tax season.

Depending on your budget I would check out a multifamily near Clarksville (army base) or an Airbnb in Gatlinburg (year round season and 10% cap rates) 

The 5% down loan allows them to go the conventional route and most are skipping home inspections and have agents who are unfamiliar with the issues they can run into with Knob and Tube wiring, lead paint and older windows/roofs. 

I'm guessing you didn't go through insurance, but you should simply let your insurance provider know that you got a new roof (don't need to say why other than it was older). 

Does anyone has a seasoned property manager they would recommend as I enter and hopefully grow on that area?   

The management issues are the maintenance issues - older buildings just break more.  

Currently running through numbers to see what makes sense in terms of rentals and mitigating occupancy risk in the transition from on to off season. 

I'm simply looking for advice from people seasoned in this field and to try to continue gaining as much knowledge as possible.

As far as the activities available in the area, it seems like most of them would be seasonal.