The question for me is what are real specific reasons WHY this is happening in S-FL?

I have REPS by actively and materially participating in my rental property portfolio, and also work as a real estate broker full time (1099 collecting commissions through a single member/purpose LLC) from buildings I sell.My losses from my rental properties (LLC #A) largely offset any federal and state taxes from my brokerage business (LLC #B).

It is going to be near impossible to cash flow on a property with 100% financing, especially if that partners rates are above conventional rates.

You want both of them to be real estate experts so the process will be smooth. 

This property has been a great experience and we have learned a lot from it over the last several years.

Online search engines and an amazing real estate agent, who is still a good friend; she understood our needs and actively worked with us to find a family friendly neighborhood closer to work.

Hi @Dylan Fraembs and welcome to Bigger Pockets and real estate investing!

Even if a software is free or cheap, it's the time investment getting things set up and then tweaking it for the first few months that is the real "spend".

I am currently an investment real estate agent in the Middle Tennessee area, especially around Nashville!

Or maybe certain markets or property types you’re curious about?