Ebb & Flow
I purchased three of my six sailboats in recessions. Understand that if you are working at a good steady job, it's your good fortune and the recession is someone else's. I sold those boat later for very good prices, all somewhat more than I paid for them but not for what I had into them overall. They were improved from a cosmetic and functional aspect. All three sold quickly, too.
I remember people asking the same question you are asking now, as slips opened up, boat manufacturers closed, brokers tanked and suppliers went out of business. Still, they did come back.
Here is my guess: we are in a turbulent economic period and will be for another couple of years. There is a recovery underway, but people are only incrementally getting into luxury and recreational purchases ever so slowly. Confidence will build over time and the sailboat market will respond.
The new boat market will continue to compete with the used market simply because there are so many quality, inexpensive used boats in the market. The good news is that this provides an economical entry point for new sailors, more so than years ago.
Relative to demographics, there is an aging of the population which would be much more pronounced were it not for immigration. Here on the west coast, there is an increasing interest in boating generally among immigrant populations, some of it into sailing, more into power. Regardless, that will fuel continued interest in waterborne recreation. As far as younger families, I think sailing is still a valued family oriented recreational activity that will continue despite competition from other outdoor recreation. However, their discretionary income needs to build first. I do not, however, expect there to be substantial growth in sailing of larger boats, however, owing to restrictions on new marina construction, increasing cost of ownership owing to environmental threat mitigation and the availability of a large pre-owned market.
At least that's my take on it. FWIW, I was going to start a new thread on a similar topic before I saw yours. Interestingly, last year, some brokers commented on how hard it was to get listings. I thought that was just hype, but I have been trolled by no less that three brokers this month asking for a listing on my boat. I have seen the for sale ads in local periodicals vastly diminish; I thought it was just migration to internet sales sources, but something is going on. IMHO, I'm thinking that a lot of people are simply sitting on the boat they have vs. moving up for a variety of reasons.