Quote from @Bob Smith: HOAsThey can prohibit rentals or impose such crazy regulations you won't be able to rent.They can also change the regulations....I just saw an HOA first try to implement $300/year rental registration. 

While being a full time college student and a part time boxer I've primarily focused on wholesaling, building a successful business with my best friend that did around $70,000 our first year in the business.Being from Illinois rules and regulations have caused us to pivot from the traditional assignment of contract.

I recommend getting acquainted with the tenant laws and regulations specific to your area.

Competition does a better job of regulating pricing than company transparency in my opinion.

I think Austin is pretty restrictive on STR regulations but that might not apply in your area.

(on the buyer side) or is there some regulation against this? 

Airbnb Considerations:For Airbnb, make sure to check local regulations in Tampa regarding short-term rentals.

The extreme tenant friendly laws in Ontario and increasing regulations for short-term rentals are additional reasons why I do not find investing in GTA no longer viable.

There are very strict regulations but possible. 

But I would like to use my chance to comment on this to emphasize how much of this situation really reflects on how you've managed the landlord-tenant relationship to date.In a high-regulation area-of-operation like California, cordial landlord-tenant relationships will get you past a lot of garbage like this.