-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.

Owner/occupants also have the option to make their buildings "active" and use the large losses created by cost segregation and compliance with the Tangible Property Regulations against the business income.

Does anyone know the rules & regulations surrounding short term rentals in Douglas County, CO and if they are strict to enforce any such rules?   

Unless you are buying a chain with a national advertising campaign (Like MCDonalds), or some kind of government issued license that is hard to get (Liquor License) Or even something like mineral rights.Other than those few things, you're buying a lot of hot air.

It is a rare break in favor of individuals in an overly regulated state.