This works really well especially for BRRRR's because you can cash out refi.  

Is this the only market you are looking at to invest in or are you open to out of state investing as well?

Its both asset protection , business planning as well working towards getting REPS status for tax purposes.

The biggest question I would ask is how well they know the area such as neighborhoods and do they have connections to building a CORE 4 such as great contractors, property managers, attorneys, etc

(This includes character attacks as well.) 

I am looking to purchase real estate for both investment purpose as well as to offset as much tax liability as possible. 

It is a well documented and classic grift.

We have owned a STR in Florida's panhandle, which has done very well for us for 10 years. 

I was going over his financial information and saw that the guy was making over $50,000 a month and asked him what he did.

Your new place should turn into your new business location as well.