My biggest objection to this deal is the low cash flow with the high debt. 

You have principles in more than one state, so securities laws in both states may have to be dealth with. 

Can I itemize mortgage interest on all main homes in 2017 as long as I only figure the interest at the time it was my principle residence?

I've tried applying the rules of thumb and running the BP rental property calculator, but at this point I'm definitely not objective.

what is your objective?

Those are all very location specific. all your other expenses appear to be in line with generally accepted principles... except vacancy.

Your main objective needs to be finding a lender that can help you pull this off.

I've tried applying the rules of thumb, running the BP rental property calculator, and talking with my agent, but at this point I'm definitely not objective and I'm approaching analysis paralysis.

If they suck this bad, I wouldn't want to give them my business out of principle

Your “debt coverage” would be interest And principle payments, so.....what is the anticipated rate And the amortization schedule, this determining your monthly Payment.