I have the chance to do this right with an investment mindset.

The emotional / confidence factor does matter when it comes to conviction to hold over the longhaul.4) Are you improving or decreasing in the quality of area you are going into in order to acheive this cashflow in PGH?

When you're listing has no reviews, at lot of people pass over it, no one wants to take the chance. 

Thats how they know your properties condition has “improved”.

Chances are you may show a negative cash flow which is throwing you off.

DIY Basement BuildoutFinishing the basement for around $25K could improve your STR competitiveness and increase rental rates.

Chances are likely nill because there are other investors involved.

You may be able to factor in certain improvements to your personal residence so when you do move out, you can be eligible to depreciate it.

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?

If there are damages, chances are you will never see the money to fix them.