There is a lot more involved in than just owning a boat and enjoying the sailing. Especially if one has to purchase a boat. I am sure you know all the nitty grittys involved but as the saying goes, haste makes waste, in this article. .
I’ve owned and operated a couple of power boats and a cruiser and was always amazed at how many idiots there are on the water. That said, when I was much younger and apparently eager to die, I did do some sailing on a friend’s catamaran a few times which totally knocked every aspect of being an aquatic idiot right out of me.
As the saying goes, "don't trust the fart." That can be extended to "don't trust somebody else's survey". A lesson learned the hard way, spoken from painful experience. The two happiest days in a boaters life: The day he bought the boat. The day he sold the boat. A boat is a wooden (or fiberglass)-lined hole in the water into which you pour money. I wouldn't have traded a moment out on the water with our many boats (OK, I lie......there were some moments I definitely would have traded...) but I'm too old for sailing any more and I don't have the patience these days to deal with a cranky stinkpotter.
If I still had my 47 foot steel hull cruiser. I do believe we’d be living on it on some river or lake. Of course, when I owned that boat Yvonne and I hadn’t even met so maybe she wouldn’t like living on a boat as much as I did. Dunno.
I am sure you may have weighed the pros and cons of owning your steel hull boat before you sold it. This is the time when one wants to be laid back and not have to worry about their boat running aground, or any other boat issues. On the other hand that's what cruises are for. Or there is always the option of a small paddle boat in the middle of a lake waiting for a fish to bite, as a pastime.
The largest problem with owning a large boat of any kind is moving the derned things on land. I lived on Watts Bar lake and also on Lake Mead and owned boats at each location. Each boat was part of a kind of tradition. Because of the expense involved with moving the boats any distance and the immanent repairs that would have to be done afterward, the owners sold them. When I was ready to leave Lake Mead, I too sold that one and when I left Watts Bar I sold that one just like the previous owners. Alas, I did know what I was getting into when I bought them especially the one I bought on Latke Mead. Much to the chagrin of a few who brought their huge boats to Lake Mead they found that it is one thing to bring a cruiser or yacht down a mountain to a lake but quite another to take it back UP the mountain when moving. Some boats both sail and motorized are even abandoned and can be bought by simply paying the late slip fees.
We used to get with 1 or 2 other guys and rent a 21-25-foot sailing sloop, which we cruised in Los Angeles Harbor. "Stand by to come about...Starboard Tack..." "Got it, Skipper! Coming about now...watch the boom swing!" (We made it a point to steer clear of the "Stink Potters", who know little about making the wind and the currents work to their advantage.) Hal
Plenty of people live on boats in Florida. We were pretty amazed at how many do. The sailboats were moored and the big cabin cruises were docked in a rented space. The owner of the Jacksonville Jaguars (NFL team) had his huge cabin cruiser tied up at the The Landing on the St. John's River. When he wasn't using it, he would lease it out. We seen it.
We've put plenty of money into our 1992 20' Celebrity Cuddy Cabin. But, like anything else that is "fun", it costs to have. It's got the largest V-8 engine (5.7L) Chevy that can be put into a 20' boat. Bought it in Jacksonville in 2009 from a Navy Lt. Commander stationed at Jax NAS. It does nicely on our local lake and is easy to launch, since we had an electric winch put on the trailer.
I had a ski boat for a couple of years in my 20's but got tired of it because it was hard to find a driver that could stay sober and take safety seriously. Most in their 20's saw a ski boat as a party tool. I sold it and bought a 16' sailboat that I could sail by myself. It was fun for a while but then became boring. I made a spinnaker for it but running up and down the river became tricky as the number of windsurfers was increasing. I sold it and bought a couple of sailboards that I had for several years before kites replaced sails and boards were shortened. I lost interest and I gave up being on the water after I discovered a remote lake that had a no motor rule and wasn't exciting enough for the kiters. I was hit by a sudden unexpected gust of wind that picked me up and blew me sideways for several yards before wiping out. The current and waves washed me to the far end where there were large rocks and rattlesnakes. It was an area known as rattlesnake heaven. I had a half-mile of jumping from rock to rock and finally stepping carefully among the sagebrush before reaching my pickup. I saw several snakes. Luckily they didn't feel threatened by me. I hate snakes especially rattlesnakes. I thought of just leaving the board, mast, and sail, but it was worth about $3000, so I waited out the storm and then used my other board with kayak paddles to paddle down and tow the board, mast, and sail back to my pickup where I loaded up never to return. I sold it all the next day at a friend's flea market booth. I was offered $2000 cash and I accepted. Circa 1980.