Does anyone have suggested property management companies they've used in Florida that they can recommend I reach out to, to see if we're a good fit for each other?

Single-family management companies are seeing interest from buyers.

Fannie Mae will allow you to transfer the deed to an LLC if you decide to try to go the conventional route, but the loan would still be in your names and you'll need to pay a title company a second time post-closing to do this  for you. 3) I can't speak for the area so no comment there4) If you're self managing, make sure you find vendors you can trust in the area since you won't be able to easily verify if an HVAC guy, plumber, etc. is trying to rip you off and tell you to buy something you don't actually need. 5) Make sure you have clear alignment of goals and a clear operating agreement that spells out what to do if those goals start to not align in the future since you'll be jointly obligated to these properties. 

Cash flow is definitely the biggest challenge; both in terms of finding properties to buy that cash flow with a loan on them and just company wide given interest rates and labor/material is up and, at least where I'm at in Jackson County, MO, taxes are way up too. 

Here's an article with things to consider when selecting a cost segregation company.

Sounds like your 2 previous companies didn't know what they were doing.

Very different from a typical insurance company. 

However, the average lifespan of companies is 10 to 18 years, so every private-sector job your tenants have will eventually disappear.

In those cases, the title company guided us on the necessary steps to resolve the title issues, and we did whatever was required to close the deal.

Call some local HVAC/Mechanical companies and ask what the average cost would be for this upgrade!