To be honest I doubt I'll face the 'everyone wants to go' scenario too much. I swear a large family is an awful lot like herding cats! My Admiral is very comfortable commanding from the home office, and my teen, who built a beautiful wooden skiff in a seventh grade extra program, is now firmly in the hormonal angst stage. So the normal thing I see is me with a couple of kiddos along 80% of the time.
@Captain- My 20-year sailing gap has been due to three things: job, babies, and debt. I took a new job a few years ago, my babies are all in school now, and as of last July I am completely debt free.
I would say sailing opportunities are 3/4 of weekends, and if I snag a spot at one of the marinas 15 minutes from home, a possibe dinner sail (My work hours are offset on the early side...normally I am home by 4pm to handle winter after-school activities).
Actually now that I think of it. I'm sure I read advice in another thread along the lines of buy the boat that fits your everyday needs. Charter for the big trips. Might that be a good option? A single-hand capable boat that fits 4 of us, and if we want a full crew vacation then charter something big enough for that?
I'm not too keen on racing. Although who knows? We could try it and be hooked.