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. 

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

Always get multiple opinions

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

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

As far as the attorney goes you may have multiple. 

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

Most deals are still being marketed to multiple buyers.

Mine is taking multiple months to find tenants and overcharging sometimes over 300% on maintenance calls from crooked handymen.  

My biggest hurdle has been securing financing to work on multiple projects simultaneously.