I picked up the BRRRR method book and feeling confident in setting it all up (we did a similar process for our Airbnbs).  

For property management, I am personally a fan of managing your first property (with proper education or mentorship before beginning) since this is where you will learn first hand what is required in managing a tenant.

We have had work crews from a local lab and solar farm (separate bookings, obviously) for 3-8 weeks that rent the whole house in the offseason.

After that I would read every single book on fixing up properties that you can find, and how to find off market properties and then start implementing those strategies.  

With the use of VRBO, Booking.com and direct bookings can all raise your chances of staying booked and being successful.  

Most of the STRs out here in Hawaii are sold turnkey, so already furnished and decorated, many with lots of future bookings. 

What is their book of business?  

I’ve read a couple books but I am always willing to learn… Also if you were 21 , what would you have done differently?

Read a book, or even a blog like this one:  Application Screening GuideIf the landlord had called the previous landlord (me) they would have immediately denied her."

Also, for me 30+ bookings tend to be less profitable even though there are less vacancies.