I love sailing. I've sailed for 45 years now. I've owned plenty of powerboats too but it just isn't as much fun for me. Powerboats are easier, yes, but after roaring around in one, unless you actually have a destination, some place your are trying to get to for a particular reason, it just gets old for me. Sailing on the other hand certainly allows me to get to a destination if I want to also. But just sailing around never gets old for me. Maybe it is because you have to work the boat to make it go, not just turn the key and push the throttle(s) forward. You have to constantly watch the wind, your heading off the wind, the position of the boom and the sails and keep her trimmed. Currently I live in Phoenix but my brother and I share a 60' sailboat that is docked at the Southwestern Yacht club in San Diego. Some day I want to retire and live on that boat and at that time I will buy my brother out. He and I get along really well and have never had any issues with co-ownership. We split everything right down the middle, boat payments, maintenance, dock fees and the minute amount of fuel we do burn that we use to take the boat in and out of the harbor. He lives in San Diego, LaJolla actually, he's a Captain with Northwest Airlines), Sailing along with only the sound of the wind in your sales, the splash of the water as you cleave the way through the water, pretty girls, sunshine and wind, that's all I need. Actually just the wind, the other two, meh.
We got this boat quite awhile ago when my father passed away. Everything else he had, 2 planes, motorcycles, cars, and real estate we sold off and the money went into a family trust for my brother, my 2 sisters and myself to share when we retire. We also purchased the boat (financed), and that money went into the family trust also. My father was going to sail the world on that boat but passed away just before he retired so he never got that chance. He did get to sail it alot with us and that is also a big part of the appeal I am sure.
My brother and I do regret selling off his Decathalon and his hanger he owned at Montgomery field in San Diego. The other plane was a Mooney.
The one powerboat that I really loved and miss was a '70's 16 foot Donzi with a 351 Holman-Moody. That thing was really fun to roar around in but pretty useless otherwise.