Considering I have twice the amount invested into my boat than it is actually worth, I look at sailing as an irresponsible addiction that I only value in family/friend appreciation time.
(True Story) A good friend of mine once said that any boat owner is an idiot, I looked back at him and said but you've owned boats your whole life. His response was "well I didn't say I wasn't an addict" I personally feel this sums up most of us on this forum.
Boats are for pleasure, family, friends, and chasing the dragon.
Personally I would rather die a poor boat owner than live as a wealthy person that obsesses over their lawn.
Certainly appropriate to consider owning a boat an investment. As with most any other asset of value, cars, stocks, bonds, real estate, et al, each have their own return potential. And it all has to do with how you define return. No need to tell you here about that, but with us the value investment return on adventure, freedom, friendships and exposure to a whole new life world of sailing was ample and very gratifying. Sure there was a risk in the beginning, but to us the return potential was happiness, which has an ill relation to money value. As others have mentioned, a foolish person would expect a boat's price value to increase over time, and that goes with any other asset. A wise person will select the asset most likely to deliver a return over time and if it does your risk gamble paid off and if not, well...
Were we wise in purchasing our boat in 2002? After almost twenty years it is safe to say that our investment paid off handsomely. Money growth was not on the table. It has been that anxious pit in the stomach you get each time you untie the dock lines or raise anchor and head toward the horizon that made our investment pay off. Watching the joy in our grandchildren's eyes when they had the opportunity to be at the helm while under sail for the first time, the excitement of when the Admiral made her first docking experience, or each time the rail was in the water. Those priceless moments have no cash value, but brought huge dividends to our life.
Someday soon we will need to sell our asset and that will be a sad day for us. Few will have experienced what we have and in the end, even if we donate our boat to some charity, the ample return on happiness over these past twenty years will remain with us forever. Just say'n.
Last week after our local hurricane remnant floods (pre Ida), my daughter and I salvaged a perfectly good cheap plastic Adirondack chair and a serviceable paddle boat from way out on Cayuga lake. Gave away the chair to our local eco-tour boat and left the paddle boat for the State Marine Police to sort out, salvage rights notwithstanding, but better memories can't be bought than my daughter churning away like mad at the pedals 4 miles out from the marina while I towed her in behind our little sailboat.