This will help you avoid any legal issues and ensure that you’re correctly handling the taxes.Best Regards, 

Each Housing Authority may file an Administrative Plan up to 1 time per year to modify the Section 8 HUD guidelines.

Is there any legal obligation to pay the unpaid utilities?

In Unincorporated Pinellas County it is legal. 

Cambridge regulations are similar to Boston's and I have 2 legal Cambridge listings on Airbnb.

I would 100% stay go with the professional service because at the end of the day the tenants will not repair it like a professional will but on the other hand would that be legal in your area??????

@Jay Levy that's a lot of asks and is too much to type.So, here's copy & paste from our website that may answer some of your questions:-Robust Tenant ScreeningA bad tenant can lead to thousands of dollars of losses via unpaid rents, legal fees and property damages.

Anything else will not qualify under the current guidelines.

I used Zillow to list my rental and accepted someone's application however after my few interactions with them on the phone some major red flags have come up and I wanted to know am I under any legal obligation to rent my property to this person. 

@Sylvia Kuang, you can only legally receive compensation for work as a property manage through your brokerage.