The booking habits of vacationers has changed a bit this year and its mainly last-minute bookings that are only 4-6 weeks out.

If you make it a habit to be at these and you're a familiar face it will make things exponentially easier.

Don't get into the habit of being too nice of a landlord.

I still want to learn more about trends, buying habits, supply/demand, etc. but my guess at this point in time is that this will likely become a rental property.Thank you @Chris K. for the feedback and particularly the recommendation of @Patrick Liska.

Probing is the best solution to understand the problem, might be you don't know the answer then and their, but their is no harm in saying that I will get back to you, which will give them a re- assurance that you are not giving any false commitment.

Unfortunately a new mayor was elected last year and he stopped that program and is even trying to pass new legislation that would be quite harmful to STR owners as well as most management companies.  

We don’t know any PMCs to recommend in the area mentioned, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

Between the government injection of trillions of dollars, the changing of our lifestyles and work habits, and the changing of our spending habits, I've changed my tune. 

.- Your short-term processes and habits are where you need to go from big and ambitious, to easy, attractive, measurable, and satisfying..

They claim they have had to trim the tree, resort to extensive clean-up and the excessive growth has caused vermin and other creatures to feed off the tree.I researched California tree law and learned that the neighbor has a right to trim the parts of the tree that are extending onto their property but don't have a legal claim/dispute against me unless harm is caused.