In our experience, after a certain point you don't really "need" to plan anymore, certainly not more than just making PS ahead of time (during busy times especially, or if there is something "special" we want to do) and planning to be in the area where the meal is. Heck for that matter, we tend to make PS around the area we are staying. I think we make them more for just the fun of planning. But there are a lot of days we just call from the room after thinking about what kind of food we are in the mood for.
After a while you don't really need to plan what to do when, you understand what days you like to go where, what time of days to do certain things, how to observe and understand the traffic patterns and crowd levels and go with the flow (actually, against the flow). You just know what to do without having to think about it a whole lot. Not rocket science. Everybody probably needs to read a guide book and plan out every day of a trip at first, but after a while, you just go and have fun, and if something is closed or too long a wait, what the heck, you can do it next time, you're just here to have fun. I find a disney vacation relaxing.
