If things work out with this 2nd company, and I have one operating rental in place of two empty lots in North Port, I'll be happy(ish). ya I built 3 up in the Ocala area took way longer but they got done and we did make a very small profit on them but I count that as being very fortunate.

As we have 100+ year old trees on the property, as well as a pond and year round stream, I think it could also be used for a tiny-home or tiny-office (commercial) community, which would allow me to maintain control of my property long term and providing recurring revenue to me (my company). 

You need a company vehicle for the guy to get there.

Any suggestions on solid management companies in the area?

Under this idea, you'd need to see if the Health dept has any restrictions for your septic system (which i assume you have) and if the power company would meter the 2nd unit separately. 

This was awhile ago, but in case it's helpful---There are companies that focus on supporting investors to rent by the room.

If you are working with a reputable company, then you buy the property, hold the property and look up 7-10 years down the road and have a home that has increased in value and a debt that has been reduced by your renter.   

Strong property management and careful tenant placement also play a critical role in success here, so I recommend partnering with a turnkey company or an agent who specializes in these areas to make the process smoother.As for rental demand, homes that sit for extended periods are often the result of issues like pricing, condition, or tenant quality—not necessarily a reflection of the market as a whole.

For the last 3 cities, I talked to turnkey companies whose numbers on paper looked good but decided not to go with those cities since I knew nothing about them. 

I actually hired this tax company in the Fall of 2021 to do my 2021 return and continued using him for this year (2022 return).