I do all of our planning. The first time or two, my wife thought I was nuts. But when she saw how perfectly our trips go, she was all for it. I'm pretty intense: I've got a spreadsheet I used to keep track of everything, I'm constantly gathering info, making reservations, etc. I've only had ONE time where I tried to book a resort at 7 months and couldn't do it (VGC). We decided to bank the points and went to VGF the following year instead, and she loved it, so that worked out. But I'm convinced that with such a small point contract, my vigilance in planning is the only reason why we can make it work.
I just made our reservations for Aulani in April. We have a DD now, and she'll be just over a year old when we go. I managed to work some of my own special magic and we'll be flying First Class (for less than the cost of coach!), my wife's first First Class experience!