and how do i cover this up?

Hey Dave, since I have mortgages on these properties, would it make sense to bring cash to the exchange to cover the mortgage amount (or pay off the mortgage before doing the 1031) and improve the cash flow for the newly acquired property?

There's nothing left to cover expenses so you better have deep pockets to cover maintenance, admin, turns, etc.If you think you can quickly improve rents to a point that covers your expenses and pads your pocket a bit, then maybe, IF it hits your return threshold.If you're buying cash, then the mortgage is not a factor. 

So the question is - why would someone entering a deal/assignment need a gator to cover EMD?

The idea of house hacking a multi-family property is a great way to cover living expenses while building equity.

We recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

You need to be skeptical of track records that only cover the last 8 yrs.  

@Noah Schulz what does the lease state about payment and what period the payments cover?

- Insurance policies (some may not cover rent by room)- Friction among tenants regarding common spaces

Tenant damage, beyond normal wear and tear, tends to be covered by the deposit.