Good discussions all around. I think you kind of missed my point though. Most boat owners enjoy piloting the vessel and doing all the other things like docking and anchoring. That's part of the attraction and sense of adventure and accomplishment. If you get to the point where it's just about being on the water and having someone drive the boat while you sit in a lounge chair and enjoy the view with a cocktail, there's better ways to do that than buying a bigger boat and hiring a crew. If that's what I wanted to do, I would rather travel to different parts of the world and charter a boat with crew or some sort of small size cruise ship. I think the experiences would be better at a fraction of the cost, but everyone has differnt ideas of what they enjoy, so my opinion is just that. It doesn't have to be right for you or anyone else. I don't think that's quite the same as having more than 1 home vs. staying in a hotel.
Understood and I agree. I’m thinking there might be a stage where you want to do many of the things but have someone as a backup just in case? For example, I am licensed in seaplanes but if I haven’t flown in some time I take along a professional pilot. Or on longer trips as someone to help manage or ferry the plane (ie you can’t leave them tied up at a public dock when you go to grab a sandwich).
I don’t want to distract from this thread anymore with my ramblings on the potential future I know nothing about!