Decide at the outset that Jost, CGB, and Norman island are not where you want to be with your younger one. Get up to Leverick at least, decide soon and if you think you might want a slip or dockage at Leverick, make reservations. You can always change your mind, and those slips will be at a premium by Christmas. I second the idea of Anegada for Old Years Night. The Anagadian community is beyond skilled in helping you to have everything you need, and still making it fun. That, however, is a sail leg in the BVI that warrants real-time wind and sea-state forecasts that you can't have in your pocket right now. Leverick reservations to hold your place ( and the resort does do a great holiday spread), but that's also the easiest start point for the sail to Anegada.
I might disagree with Norman being on this list. We did this a few years ago. We took possession of a cat mid day before New Year's Eve and headed straight to the Bight. Plenty of mooring balls, great swimming. Drinks at Pirates Bight, evening at Willy T's (not for little kids but this was a normal Willy evening, I've seen worse) then dinner on the boat (we'd packed Surf and Turf). The entire crew was out by 11. I was last one up and there was no noticeable noise from Willy T or other boats. Really a great night.
Dave