Getting rent paid when you look like you know what you are doing (even if you are just starting out) is much easier than if you look uncertain or disorganized.  

In the parlance of business, I'd say Colorado Springs provides an "uncertain regulatory environment" when it comes to Airbnb and other short-term rentals. 

How do you estimate for an unusually hot summer or a colder than normal winter?) 

I'm uncertain how to reconcile your statement about not having an exit strategy with my research into Sub2's.

They have an ability to find great tenants, which is unusual in this market. 

I told him face-to-face in no uncertain terms to stay off my property and I was prepared to involve authorities if necessary.As @Marcia Maynard says you will need to be very diligent about monitoring the state of the property.

That's not unusual. 

I would pass based on his refusal to provide required information, refusal to agree to pay pet deposit, sketchy situation regarding his present residence, uncertain employment and CA connections.There is simply way too much wrong with this situation to bother wasting your time trying to make this applicant fit.

Turnover is expensive, time consuming, and uncertain. 

It is an unusual here in Mississippi to have really cold temperatures.