My heart would like to let him stay for free but I doubt I can afford it and also, I’d like to make sure my interests and his are adequately protected in case this get “squirrelly” in any way.

It wouldn't hurt to make some phone calls and see what type of a response you get on how the city feels about STR. 

Thank you for your response.

You want an accountant that can help you strategize and who is responsive when you want to know the tax consequences of the decisions you are making throughout the year.Good luck in your search.

:) Consider it my tip of the day....

Thanks for the very detailed response.

Well, you will see my responses in bold that show the facts vs some guy sitting on the internet thinking he/she knows what they are talking about.

As a section 8 tenant what are their responsibilities to report issues? 

Thank you for the response and for the warm welcome to the BP community!

@River Sava Thanks for the tips!