On St. John: If Cinnamon Bay isn't your style (I stayed there for a month, and, it's camping, but fun, nice people, possibly too many kids) I'd suggest renting a condo if you're not going with chartering a boat. You can get pretty sweet condos for around $2K/week. They're not water front, but, with a rental car (watch out for Donkeys) it's not a big deal.
If you're there over New Years absolutely don't miss the New Years Eve party on Jost Van **** (it's on the BVI but they have boats that make the run for new years).
If you win the lottery
http://www.caneelbay.com/ is where you want to stay.