I just went from a 33 footer to a 41 footer for the purposes of passagemaking. I couldn't see me, the wife and our son, who will be eight when we leave and maybe 13 when we return, on a boat that wasn't essentially "compartimentalized" into deck, aft cabin, pilothouse, saloon, and forepeak workshop, which, currently accessible only via a heavy steel deck hatch, would make a nice sulking place if needed. The up/down nature of the boat further sub-divides things into distinct "zones"...I'm not even counting the head.
This was very deliberate a consideration as we were boat hunting. We wanted a small by current standards saloon for safety reasons and we wanted sea berths in that saloon. We wanted a pilot berth, or at least a place to curl up, in the pilothouse if we needed "spelling" during a watch. And I needed a place for my books and to write, which meant a folding office table in the dark and quiet aft cabin. Wait until I put crash doors in...it will be hermetic...
All this is going to be, I hope, vindicated during long passages when we might want to get away from each other a bit. But I don't think it makes for a great Lake Ontario boat. For that reason, I am in essence leasing my old 33 footer to a friend for a number of years, because I want to have the option of selling the "expedition" boat when we return and going back to the stripped out cruiser. My larger-boat-owing friends can't believe I'd ever go back to a smaller boat...and 33 feet isn't small, but it's smaller than it used to be...but I think I want to at least keep that door open, as the strengths of the smaller boat for all the Great Lakes and even doing coasting in say Nova Scotia to Newfoundland are more practical than maintaining an ocean-ready passagemaker. It's like those miniature panel trucks the post office uses to drop bags off to the mailmen: they are just right for the job they do.
Besides, I really do prefer the tiller to the wheel. I guess it's like when you love a petite brunette and a tall blonde...why choose when you can love both?