Property was sitting on market and needed light updates (roof, flooring, paint) but was in a great area that allows STRs giving me multiple options when deciding on rental strategy How did you find this deal and how did you negotiate it?

Put language in your lease about use of the screen for all fires.I always made it the tenant's responsibility to have the chimney cleaned at least once per year for the built in fireplaces and twice per year for the store bought types as they have smaller chimney piping.  

We could have saved some money starting to clean up the property if we had only checked in with the neighbors first.

Renting out a room is a great way to get started, and I wouldn't get too settled into the "going rate" use that almost as a floor. 

I’ve helped several clients in similar situations find their first vacation properties here in Florida, and the Panhandle is fantastic for beginners because of its year-round tourism and robust support networks (property managers, cleaning services, etc.).

He recommended we do some work to move the outflow from nearby downspouts further away and then clean/reseal the interior wall.

It is entirely possible to self-manage with a strong cleaning team.

That hard work includes making the investments that the current owner hasn't made (nicer kitchens, new flooring, fresh coat of paint, etc.), removing tenants and marketing to new tenants.

Additionally, consider operational costs like cleaning, staffing, and marketing, as they can quickly add up.For management, outsourcing to a professional property manager or leveraging tech platforms for bookings and operations could streamline things, especially if you plan to scale.

i.e. paint, flooring, cabinets, tile, etc.