I've been thinking about this thread in context of my boat. Some background...
Pre-mustachianism, I owned a small (25 foot) sailboat in a local yacht club. I paid about $400 a month in slip/storage fees (annualized) and had an annual maintenance budget of around $2500 - $5000 depending on what went wrong (a new mainsail = $2500, an engine rebuild = $1,000). The boat itself had a bluebook value of around $6,000, but book values on boats are pretty crap. Its hard to find a buyer for a sailboat, so folks end up giving them away cheap. I sold mine complete for $2500 once we got serious about stopping the holes in our budget. Parting it out I would have made more money on the sale, but that would have meant paying storage longer.
Anyways, I went out every Wednesday night for race night, and a couple weekends a year for cruises/regattas. I loved the boat and had a lot of fun on it. My wife hated it and refused to step aboard, and the kids were ambivalent. I got a lot of happiness out of it while I was on the water, but the rest of the time, it was a thorn in our side. But I still loved it. The boat is the only thing I look back on with regrets since we made wholesale changes and stopped living in deepening debt (still digging out of that hole).
The boat was clearly a money-hole. But it made me happy. Many folks will say 'go sail someone else's boat and avoid the costs' but its not the same as being master and commander, and you don't have the same responsibility and decision making powers.
But... every month we are now paying down debt at a ridiculous rate, and I no longer carry the stresses of ownership, and my marriage is better for not having the boat in the background. Plus the savings allow us to do things as a family that we couldn't when I was finding my fun in a very Dad-centric (selfish?) pursuit. Of course, had Momma been more involved in sailing this equilibrium might be different. I dunno.
For me this is a case of a passion/pursuit/hobby that I gave up to save cash and bring peace to the family pure and simple, and I am waiting on the right time to get back into saililng/racing and buy another boat - but only once our footing is right. We will never be a liveaboard family, and we will never sail together (Momma is afraid of boats in general), but I'm waiting. In the interim we've bought a canoe - its as close as we are getting to yachting for a long time.