I know this is not the first hand experience advice you where looking for, but hopefully it will help you, and I really enjoy their blog anyway. Of course I am looking at sailing with a family too, so it is particularly relevant to me.
That's funny I wore my Baja Haha t-shirt today. I did the 93-94 class, and that was when everyone left on their own timetable. We just kind of drifted into Cabo on our own. Started from anywhere at any time.
Now days it is a great function with huge support from all angles. They go as a fleet, and meet up to party along the way. It's not for everyone, but I can see where most would like it. Do some reading on Latitude 38's electronic magazine.......i2f