You may need a private placement memorandum or other documents to comply with SEC regulations.

Check your local regulations to see if the rental operations you have in mind might be limited by local regulation, like BNB activity.

If any of you know the legality around this, HOA regulations, any helpful documents, advice, pricing estimates, or contractors you recommend for a job like this, I would love any advice I can get. 

I've learned to set expectations about listing being in in an urban environment and the great diversity of the neighborhood. 

I think that doesn't sound like a bad idea at all, assuming there is a demand for airbnb in your market and that regulations are in your favor. 

I have been told that Centennial has no regulations at this time.

It could be in the much more informal Rules & Regulations.

I have been reading the IRS code and regulations and am not seeing any guidance. 

My community has a proposed ordinance th the City Board is going to vote on to severely regulate, almost eliminate Short Term Rentals in our town.

This legislation, if passed, would become one of the most extreme rent control and regulation bill in the COUNTRY.