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.

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. 

Always get multiple opinions

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

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

Most deals are still being marketed to multiple buyers.

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

As far as the attorney goes you may have multiple.