It's definitely one of those issues that is very specific, and would need to be worked out with Planning.

One of the other factors that kept me from pulling the trigger is that the city has never passed any real STR regulation.

You can see Bridgeport is just building in old industrial space.

There are specific rules on when rent increases can be submitted for review, but there are no guarantees when they will respond.

Specifically, I’m interested in finding carriers you might recommend could help fill this gap.Has anyone dealt with a similar situation, or do you have advice on which brokers or carriers are best suited for this kind of coverage?

In some cases that's amazing -- one part of the town gov't considers it to be a commercial lodging establishment so it's exempt from STR permitting and regulation. 

For commercial buildings, be very specific - price range, $/door max, unit count, unit mix, part of town.

I'm looking to buy a house in the St Pete market & have read zoning regulations, articles about STR (anything less than 30 days) and have discussed with my realtor.  

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

This is a highly regulated activity by the CFPB.