However going into what is normally the slow season, I am concerned about occupancy. 

Many seasoned investors are willing to share insights, and shadowing someone experienced can fast-track your learning curve.You’ll also want to familiarize yourself with the numbers behind successful flips—acquisition costs, renovation budgets, and after-repair value (ARV).

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

I even see seasoned investors enroll in the program because they get more deals faster.

May be due to the current off season.   

I have people that book for multiple weeks during season and I don't blame them for wanting a better feel of the place before shelling out $20K.  

You won't likely see an influx of renters though unless you did a short term rental during the winter season when the outage happens down there.

We have done this for over a year now and this strategy has gone really well.We are very experienced in the STR space and understand that getting bookings is multi-faceted (ie. listing photos, reviews, amenities, PRICING, description, seasonality, etc).

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.