You can leverage the first deal you bought and your experience so far, which is a lot compared to someone starting.

I was comparing large cities to other large cities.  

If it's a long-term play, the potential savings on PMI with a conventional loan could be significant.Have you compared rates for both options?

Cleveland, Baltimore, Toledo, Indy etc....You will see net population decreases in most of these areas but these are the areas where the prices are the lowest in the USA and come with rents that are very high when compared to the sales price.

any suggestions on how I should compare these 2 options?

Obviously I want to keep my costs low but still want to spring for amenities that would give me a competitive edge compared to other rentals.

What is the interest rate on borrowing compared to the rate you are earning, then take into consideration the tax consequences. 

As our team has grown, it's become easier to cover responsibilities if someone quits, goes on vacation, or if we terminate employment, compared to when we had one or two homes. 

It amazes me the nice cars, clothes, and general stuff that my renters have compared to what I own. 

Use AirDNA to get a better feel for what may be projected and then dive into Airbnb and compare to your competitors.