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

I want my occupancy (and revenue) to be maximized so, for me, it's very important to have something unique that the other places don't have so my condos will stay rented throughout the low season and in case of a downturn in tourism.

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.  

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).

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.

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

Do not wait for the 30 days.A couple of options to raise money: If you receive at any given time a return during tax season.

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.

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.