I live in the Outer Banks and own both year round rentals and seasonal rental properties.

Likely no 2)  Is your buyer doing FHA which would require 120 day seasoning if they do not have cash or are they doing conventional? 

Up here in central New York the season is short so is it worth getting involved in

Do you have any feel for whether the vacation rental market there is relatively strong 12 months of the year, or are there slower seasons?  

The refinancing R must be done after proper seasoning or holding of the property.

If you are looking at possibly becoming a host I would recommend getting a month subscription to Airdna which will give you a really good look at the numbers (occupancy, avg nightly rate, seasonality, etc.). 

My suggestions:-Have a plan for the off-season.

I tried to contact them once a month they always had a reason why it was still vacant- slow season, tax season...

We are only planning to rent the home from Memorial Day through Labor day with a couple weeks reserved for our personal family Renting it for roughly 8-10 weeks (high lake season). 

Dig in to the data, look at the occupancy, average daily rate, seasonality, regulations, etc.