You would have no problem buying/moving any boat to the east end to live aboard. I met a guy that lived aboard east end and worked in cruz bay. He hitch-hiked every day to and from work. Said he had never been late to work in a year hitch-hiking across the island.
As far as cruz bay, you won't get in there with a new boat for liveaboard unless you pay-off someone.. too small and too full.
It's a top island on my list but I don't think I would consider taking kids to school there.