Suggestion; have lofty goals, but enjoy the ride. 

If you are struggling to find deals in your market, but have the capital and drive to obtain another property, I would research other markets based on your desired outcome- ie, midwest for cashflow, coasts for appreciation and desirable vacation destinations for STR.

@Ali Boone Enjoyed the 20 points you make.

The planning department estimates it will pass sometime in March 2022.The planner wouldn't share actual language with me, but said, "We don't want to over regulate these uses," and shared some details of the draft:No limit on the number of STRs an owner can haveNo limit on nights rented as an STRNo cap on STRs based on geography.It's just nice to have a few more options for those looking for a full-time vacation rental investment or a second home in the Denver metro area. 

What if I have a new tenant lease agreement to move in on Jan 1st, but current tenant won't vacate on or before Jan 1st due to something going on for whatever the reason? 

Every market where Airbnb is plausible is seeing a boom in Airbnb's, especially popular vacation markets.The real question is - "can you beat the competition?" 

I would definitely enjoy telling you about my experiences purchasing investment properties out of state that generate cashflow.

I have been involved with both the vacation rental management and second home real estate since 2006 here in Galveston.  

Though I enjoy my job on a creative level, I have never been the one to want to work a 9-5 job, creating wealth for other people, I always have had an entrepreneur mind set. 

Or just see if they’re willing to vacate the property and move on.