“You have to be at peace with the fact that something might happen, and you might not make it through,” says Alexandra de Steiguer, the caretaker for the Oceanic Hotel, in Brian Bolster’s short documentary, "Winter’s Watch." De Steiguer has spent the past 19 winters tending to the 43-acre grounds of the hotel, on Star Island, which sits 10 miles off the coast of New England. In the long, wintry off-season, she is the island’s sole inhabitant.