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

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

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.  

After sweating out the three days in Melbourne, Australia and doing the do we, don't we dance the entire way, we finally bit the bullet and took the plunge, along with probably 30 other people … almost 50K of hard earned cash went from our account to theirs and 3 months on, we have nothing but confusion and a horrible gut feeling to show for it.So far we have had one personal, one on one conference call, our second one has been cancelled and will now be a one way group conference where we can't ask anymore questions.

There's another slew of agents saying to re-list in March due to seasonality while that point is both true and false the agents have zero problem with some forms of manipulation of the market.

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).

Those seasoned 5+ years and doing what you want to do can be a stepping stone until you can go bigger and hire an expensive mentor.

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

Oysters have been killer this season.