Always get multiple opinions

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. 

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

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. 

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.

Most deals are still being marketed to multiple buyers.

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

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

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

As far as the attorney goes you may have multiple.