Re: Sailing "big boats"
Think it's very different depending on the detailed specifics of the boat, the owners and the landside life of the owners. We looked at bigger and smaller boats. Saw that 90% of time the boat would be in effect singled. Either it would be me and the bride so then watch and watch. Or us plus inexperienced crew meaning I would need to be up and need to run the boat myself pushing crew aside if things got unsafe. Also things break, batteries fail, shyte happens. Our physical capabilities are not what they once were. Therefore, limiting factor was size of the main I could raise without power. If the windlass goes it will be painful.
Other problem was knowledge boat would be on slips for its first two years due to landside issues and they charge by the foot.
Split rigs are a joy but not as weatherly, more to maintain with more expense and complexity. Nothing like jib and jigger until you have two sticks to maintain.
Size is wonderful but I've had my scary times with centerboards and hate maintaining them so wanted a fixed keel. Then size means more draft and the first two years are eastern US seaboard/Bahamas so decided no more then 6.5'.
Seems as waterfront gets exponentially more expensive finger piers get closer and closer together. Even some fuel docks have no margin for error. As size goes up the in/out of harbors becomes a white knuckle affair for me. Prior poster mentioned boats not going out. Personally at my level of skill I have no issue singling my boat in any weather but still need a hand ( unskilled newbie is fine) to be a line handler going in and out. When its windy been known to anchor, launch the dinghy, pick up anybody to handle lines and then go in. Think with just a bit of fore thought any body can sail a big boat. I've sailed 86' without issue. Hydraulics are wonderful. But I think it's beyond my skill set to deal with anything >50-55' near the hard edges. If your only swinging on a mooring or at anchor size is a non issue and bigger is better. If you cruise in a deep water area size is no issue. But for most of us either due to finances, physical capabilities, absence of crew being a double handed couple or cruising region 40-50' makes a lot sense.