I love your goals. We can't even decide what's next in theory, so I can't even start to work on the points. Africa is on the list (but less likely than some other options) so I'd love to hear what you are planning. As for the Galapagos, a friend sailed SilverSea and loved it, but it was cash and expensive. I saw that Celebrity has a very small ship out there that could perhaps be booked with points, but I would think that Lindblad would do the area better.
You're going to have so much fun. I loved those preschool years so much - there is so much to see and do and learn and experience.
Love the Kauai Hyatt. We've spent quite a few vacations there and it never disappointed.
If you're paying attention, you can tell when they are cold. DD loved the water but her little lips would start to turn blue (by the way this happened at swim team practices when she was under 10 also, so it's not something scary) and we could tell it was time to warm her up. I think she was at least a few months old when we first took her to a pool, but then we didn't have one in our back yard.