@Jason Muth I actually don't know what is up with Cambridge STR regulations.

Once you have a deal under contract it’s much easier to edit rather than create when you have a strict timeline.

I haven't actually spoken to anyone within the zoning offices but just from reading some of the archaic local ordinances it seems like many of the municipalities are pretty strict about retaining the aesthetics of the neighborhoods.

Fortunately, this is less of a problem today with so many people working from home.A second issue which always plagued Yonkers is that the rent regulations are (almost) identical to NYC.

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

Which, by the way, is not necessarily a bad thing if it happened.I don't see your next door house as being a rental property at any point, strictly a personal property, assuming that your in-laws are not paying you a fair market rent for it.

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. 

They are strictly looking at our income and now want to see our business tax returns.

We are planning to lease an apartment for STR Airbnb in Denver next month, but we researched on Denver that is very strict to allow only one primary residence.