Hey @Graham Huber here's a couple charts on Philadelphia compared to other nearby major cities.

There’s likely a carrier that’s most aggressive in the city where your 4 unit is located and comparing your premium to that of similar properties  nearby will be the most accurate assessment and point you in the direction of the most aggressive carrier.

Try to find a local, trusted one in Tampa or nearby area. 

My STRs will have only 10% of leverage, meaning 90% down and therefore let me take the opportunity to put only 25% down without a personal guarantee on a (nearby) property I am also investing in.

Are there other STR markets you're looking into or even other counties nearby?

Most enticing is it is located on a very well established street with a wall score of 92 - lots of restaurants, bars, shops and a park nearby.

Alterations to the original building plans, however small, can create risks.In a nearby county, they have inspectors going around town to check for any unauthorized alterations, A co-worker had an old window AC, his wife was tired of not able to open and use that window, opted to buy a through the wall AC.

And lastly, I search FunishedFinder listings nearby, find comparable properties, and track the listed rent for a few months (does it increase, decrease?).

I would say take a deeper dive into the nearby product and see if there is a premium in rents for a duplex unit versus an apartment.

You don't have the luxury of being nearby, so staying on top of things is more arduous.