I'm just hoping I can handle it until I have a salaried employee at a fixed cost to handle the busy work.

You connect with a team that will handle it all for you.

Not sure how that should be handled if it's not the tenants trash ending up outside. 

Build a Strong Virtual TeamLocal Boots on the Ground: Having someone local who can handle property inspections, meet sellers, or take photos is essential.

I have a portfolio of properties (more than 20 units) that are being handled by a single property manager. 

From my understanding, the company renting/running it usually would act as a live-in property manager and would also handle the modifications.

It's tough to find anybody from the city who knows for sure what the rules are and I get the impression that the city is still trying to figure out how to handle STRs. 

really its just how commerical real estate is handled  every deal there is a commish negotiation.

What kind of rental criteria do you use, and how do you handle folks with dubious credit history?

Hey @Eric Garces, the first steps I would recommend as a new investor is to get a handle on analyzing the income, expenses and ROI of these properties in Bridgeport.You can use the Bigger Pockets calculators to start.