But I was concerned with how high rates are now and renting it out with negative cash flow in the future. 

But they should generally at least know that limited partnership K-1 tax losses can't just offset your W-2 income in most cases, it would be concerning if they don't at least know that. 

As far as I cam concerned TV's are sold with a stand.

The only concerns that we have are insuring older non code homes and Flood Insurance.  

It's much harder to deleverage in a 1031, but you're in a good enough equity position that doesn't seem like it's a top concern here

STRs are a double edged sword, and while I understand the concern about affordable housing, it's actually the tax dollars from the STRs that fund the affordable housing communities on our island.

Knob & tube is okay if it's in good shape but the concern would be if it's a 60amp box or 100amp.

To that point - does any of the software have an app that accompanies it? 

But, he seems very concerned about the prospect of doing Cost Segregation for the depreciation on these two properties.

I'm happy to provide clarification and address any concerns you may have.Dom, I want to be like you and @Chris Clothier when I grow up lol.