There are regulations but there are ways to get around them as well. 

Not perhaps the usual purpose for that, but it was a mechanism to allow me to withhold and pay taxes and UI (my wife is a Schedule C filer with one employee so I am very familiar with the tax withholding and remittance to the government processes).They averaged about 35 hours of work per week (some weeks more than 40 and got overtime, others less) while they were there. 

I have looked at Colorado Springs STR regulations. 

Just becareful as once you "scale" this idea, I THINK you can run afoul of the Security and Exchange Commission (SEC) since it becomes a syndication or some sort of regulated investment product. 

-There are specific laws that govern short term rentals in multiple places throughout Florida, and anything within an HOA restricted community will likely have a complete ban on anything less than monthly rentals.

The Underwriter is correct you cannot get an owner occupied low rate government loan on a house that you cannot owner occupy.

And always, of course, the kind of people who tend to work for local government services here are really good at kissing their boss's butts and very little else, so mistakes/oversights/imbroglios/cluster****s happen all the time.

Navigating the Nashville STR market has been interesting so far due to the regulation and having to keep the zoning in mind.

Each island (key) has its own specific STR rules and regulations.

Keep in mind over the last year that for much of that time you were prohibited from charging late fees if the property is under a government backed loan program.