We are working with a consultant on staffing and regulations. 

And it's worked for generations and the wealthy for a very long time because mutual insurance companies understand the human lifecycle quite well (law of large numbers), they're well regulated, make safe and sound investments and in several cases have paid out dividends consecutively for over 150 years (Mass Mutual, Lafayette Life, etc).

Because of the location, this is permissible per county regulations, even though the residential neighbors are having a tough time with it.So, we have to move and convert our home into a STR (we cannot sell the property because it is 2 homes and an elderly family member lives in the other home and cannot move).  

The subsequent item you reference is "self-employment income" for purposes of self employment tax under Sec. 1402. 401k has its own definitions and regulations, which are related to - but independent of - those referenced. 

Water Supply Company is private and owner doesn't have money to build more wells and is already in some big dispute with state regulators.   

Is property management regulated by the real estate commission in CO? 

Create your own list of rules and regulation.

Be sure to check with someone that knows the local STR rules and regulations to make sure you can legally do it. 

The regulations vary by county so, so yes- do your homework. 

Operating in Philly can be a big problem if the laws and regulations are not followed to a T.