There is no rent control in the city and assuming the tenants are not subsidized you are able to increase rents to whatever your heart desires.

My heart is telling me to sell but I already have 4 other rental properties with mortgages on them. 

You are truly a wonderful person @Caleb HeimsothI have the same sized heart as my tenants.When a tenant say "My rent is late because..." it is an attempt to manipulate you into not assessing a late fee.

I've been employed for 4 years and with my overtime rate, it usually ends up at around 100k per year.House #1At 24, I used an FHA loan to purchase my first house 220k (three family) in the north end Bridgeport, CT (within a mile of the ever growing Sacred Heart University).

The purchase price of the property can by itself define your deal as a good deal or a break-even or losing deal.This thing is not for the faint of heart and at some moments you will think that you spend all your money and 6 months of effort to break even.  

, but my goal is to generate passive income through investing in Single-Family homes and renting them to people that were credit challenged in the past, but have made strides to be more reliable (my heart is in helping others).

I can assure you if this is first rodeo, value add is not for the faint of heart and requires a lot of time.

A sure way to get heart burns.....

This should give you a better idea of what to expect... https://csrmarine.com/rates/And if you want to carry passengers... https://www.uscg.mil/pvs/SPV.asp

All very good advice and confirmation of what I knew in my heart.