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

If you are seasoned or have a lot of capital, there are much bigger players you can look at.

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) 

Looks to me like we've got a case similar to that of Clayton Morris......All sizzle, no steak. well his profile looks like he is a major player in Cleveland it would be odd that your paths have not crossed.  

For seasoned investors in Cincinnati, what does this realistically allow me to consider, if thinking about the BRRRR method or other strategies?

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

Especially going into the snowy season.1st floor leak is suspect for sure. 

Rent being $300 more than PITI is not cash flow of $300/month.And the $2400/month cash flow is probably a short term rental that started in peak season.

Sometimes players need physical therapy (rehab), some need more 1-on-1 coaching (optimization/advertising) and some to be traded (1031 exchange).

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