The LLC for the property management business and LLC for the STR business makes sense, and if your looking to scale this is a good "top level" that can own properties underneath it. 

I've seen some reports saying new supply for that 2025-2028 range will drop below the levels of 2015-2018 in many markets in FL but I don't have actual sources and changes in different markets and areas. 

I'm not sure if you're OOS but definitely fly to Indiana or Ohio multiple times and get to know the areas on a detailed level before making offers.

A split level ranch in a standard neighborhood doesn’t cut it anymore.

You can identify the hotspots for crime, school levels, income levels, where there is dilapidated homes, then based on the age and condition of the property gauge where the property stands in class, happy to talk further. 

Are you looking at full gut remodels or lipstick level renovations?

Hi @Allen Moore, I’m my experience with renting SFH’s in the Chicago suburbs, section 8 tenants have worked out way better for me than market rate tenants in terms of the duration of the tenancy, the rent level and the collections.

Leveled with a skidsteer.  

In you are wanting a high level of service on both your buy and sell I'd encourage you to look the boutique route. 

There are different levels of feasibility you can order but it will be roughly $4k for the initial study and another $2k to dig deeper.