It is pretty easy once you understand the process and regulations.  

It is best to confirm the rules and regulations with the HOA directly.

Also what to look out for in regards to possible laws and regulations. 

Health hazards, like excessive dust, likely won't comply with regulations.

I have cause to evict. and here is something I just ran across: "To regulate the new moratorium, federal officials say tenants can be fined $100,000 for lying on their declaration forms, Bridge said."

So definitely check out those local regulations.

Ideally I would advertise this property as sleeping 12 (which it could easily) but regulations say 8 max.

@Rojo LewisYour contracts will dictate (and local law/regulations).

Also be aware of all the various regulations for door/ window alarms etc. required for having a pool. 

They would be heavily scrutinized by their regulators for doing so.