I keep my boat at the last marina with de-masting facilities on the southern end of Lake Champlain. The waterway serves as an access route to the Hudson River via the Champlain Canal, and thence the Intercoastal Waterway, which in turn leads to the Gulf of Mexico and the Caribbean. The route serves not only the US, but also Canada as far west as Lake Superior.
The marina owners claim that in years past, they would demast over one hundred boats that were headed south for the winter, and re-mast an equal number returning in the spring. This number has decreased to a relative handful. New York State has begun curtailing the Fall schedule on the locks because of declining user numbers.
I had a conversation with a dealer who focuses on trailable sailboats 20' and under, as well as paddle-powered craft and small motor boats. He claimed that in the years he's had his business, he's seen a sharp decline in sales of boats capable of even weekend cruising. People that are interested in the water are satisfied with spending a few hours, and then returning to the land of wi-fi.
The vessels that get the most action at our marina are those with the simplest sail plans. Two catboats go out frequently, as well as a Drascombe Lugger. The thirty-plus foot rigs with multiple headsails spend the season largely at moorings, although a handful head south for the winter. Our aging boating population would benefit from re-examining their rigs. While a Marconi rig might give a few seconds edge on a triangular course around the buoys, traditional rigs such as the gaff, lug, and of course junk rigs pay fairly large dividends in ease of use in actual cruising.