Also they are under the rules and regs of the IDFPR (Illinois Dept of Financial and Prof Regulation). 

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.

When a hypothetical comes up, you should think about the situation, consider the best way to respond, and then develop policies and procedures to deal with it when it does happen.I use a "Remove Tenant Addendum" and require all Tenants to fill it out and sign it.

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. 

@Ryan Rogers I'm not an expert, but I believe syndication is typically for large deals and involves lots of regulations, lawyers fees, etc.

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 would spend your time learning how to manage, developing policies and procedures for managing and handling problems, and preparing for the growth to come.