Re: Sailing "big boats"
I used to watch the reviews and walk the boat shows just sort of looking at the big ones with curiosity, not really thinking about them personally.
Now I've reached a point where I could afford a much bigger boat and I've looked at big boats more seriously. Doing so, I've realized how much it would diminish my pleasure. Owning and running a 50' boat has two options. Either you do all the work yourself, in which case it's a tremendous amount of time and effort; OR you hire out much of the work. When you hire it out you don't really get to know the boat. It's not personal. It's not "your" boat anymore. Same thing with having a captain working for you to run the boat.
I used to think I could never have a 50+ boat because the operational costs are 10x to 15x what I currently see. Now that I can almost afford to piss away an obscene amount of money I begin to realize that it's not about the money. It just would not be as much fun. It turns into a management task, coordinating crew, reviewing plans with marina staff, scheduling dock space. You cannot just show up anywhere with a 55' boat and expect to find dock space. I don't want to do planning, I just want to go sailing.