There have been multiple revisions this YEAR alone for state regulations that most leases online will not have updates on. 

.- The numbers may have an impact on your decision.You may also want to read your condo's Home Owners Association Master Deed & Bylaws to make sure there are no restrictions on any type of rentals. - Many HOAs have LTR restrictions and some now have implemented STR restrictions.Also, hopefully you've updated the home insurance policy of your current STR rental from a homeowner's policy to a landlord policy.

We own multiple commercial properties in our portfolio across several states (both local and not local), that we self manage, so that part I am not worried about at all.

Here's my primary reasons:Expenses disproportionately impact lower rent collecting properties For illustration purposes compare two identically designed 1+1 duplexes in the same 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.

Understand its impact or know ways to by pass the seasoning.  

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.