I was on the phone with the Maintenance Coordinator multiple times asking what was going on and if the tenant was breaking things or was it my fault as the owner.

The 1031 exchange would allow you to indefinitely defer all of the capital gains taxes and use it to purchase multiple newer properties with lower capital expenditures, in a better market. 

A lot of them get multiple phone calls or letters in the mail but just keep in mind when you use a Big Bank (FDIC) you "Do not" pay points.

They get multiple quotes for work, provide honest feedback, and pricing is within line.

My challenge is that I’m struggling with figuring out if a property will be profitable or not, even though I've done research on sites like AirDNA and tried to analyze multiple factors.where Im stuck: 1. 

You can exchange 1 property into multiple properties in locations and any asset class (farm, office, single family, multifamily). 

Always get multiple opinions

As far as the attorney goes you may have multiple. 

I am in Pittsburgh and there are multiple large hospitals within 15 mins.

hence, your strategy is good for you but doesn't make sense in an economic stress test to a lender.