I know of people who own several boats. They are boat junkies. It is impossible for their owners to sail them all, at the same time! Choices have to be made as to which to sail, and time has to be found to do it. Costs of ownership escalate, and maintaining a personal flotilla can become a nightmare on account of the effort and expenditure required, especially if they are of the wooden variety. Fibreglass vessels are not maintenance free, as one may suppose. Whatever the vessel, if she deteriorates, her value falls; in the extreme, she becomes a liability. She cannot be sold; no one wants her. Many such vessels litter boatyards and dumping grounds at sailing clubs.
To me, it makes a lot of sense to own one, or perhaps two boats at most. I can see the merit of owning a sailing dinghy and a sailing cruiser; the former for impromptu outings, and the latter for planned trips and cruising excursions, including one or more longer cruises. There may be merit and justification in owning a specialist boat, such as particular class for racing, as some sailors like both cruising and racing.
Boats can be seen as investments, but more often than not, they lose their monetary value over time. However, there are certain makes of yachts that appreciate as the years go by. They can be sold for more than was originally paid for them. An increasing monetary value does not constitute the only true investment; another can be found in enjoyment and satisfaction through use of the vessel. If there is no enjoyment, no fun in ownership, and worse still, hassle - time and money have been wasted! Fun and enjoyment brings wellbeing, which adds years to ones life. Sailing is a health-giving activity, bringing benefits in terms of exercise, both for the mind and the body. You can go to work on a Monday morning with a grin, and a glow on your face is there to be seen by all. You can’t wait for next weekend when you’ll be on the boat again, and you are looking forward to a month or so, when that special adventure, the summer cruise will begin.
On the sober front, boat ownership brings responsibility. You are responsible for all aspects of boat management. Is she insured? Is she seaworthy? Am I fit enough and skilled enough to handle her? Can I look after those who will sail with me? Have I made out a passage plan? Have I fully prepared for possible eventualities? Taking a boat to sea is a responsible business. Forethought must be given before leaving the mooring. What is the forecast, and is there a bolthole if things get nasty? Do I know the rules of the road at sea, and am I confident of handling an emergency situation if it should arise? Am I competent at handling the VHF?
Owning a boat can be a joy, or it can bring hell, but much will depend on your judgment and choices made.