Anyone have any tips to balance the obsessive plan freak in my head and my desire to throw caution to the wind?
Plan your mornings and maybe the last hour or two of the day, and leave the rest open. The first two hours or so of the day are when planning makes the most difference in terms of how many rides you get/characters you see. Get the ones that'll develop the worst lines done then, and you'll have more flexibility later.
Alternately, let everyone pick one thing per park or per day that's the most important for them, and do those things the first few hours of the day, and then go with the flow.
Hopefully, if you can convince your obsessive plan freak that you have a plan for the time that is most important (or the things that are most important), it'll be more mellow about you throwing caution to the wind and going with the flow part of the time.
Not sure how either of those will work, since I don't share your inner conflict.
My morning is planned out in fifteen minute increments, often as not, and I have a pretty solid outline for the rest of the day as well. But even at home I don't like to go to a restaurant without having a good idea of what I'll order before I get there; I
like planning, and I like following a plan, and with five kids and a hubby who hates planning ahead, I don't often get the opportunity to do so! I don't insist anyone else follow it (when the kids were younger they could follow my plan or hang out with dad), but I always have a plan.
Particularly with a Disney trip, planning ahead that minutely means I have to grapple with the fact that I can't do everything I want to do way ahead of time, so when we're actually there and plans go south, I'm already in the mindset of, "Can't do everything, so just enjoy what you get done," and I can go with the flow. And, as others have said, planning means I've got a lot of research in my head about what I want to do early in the day and why. So in a sense, obsessively planning actually makes me more mellow about abandoning the plan.
I think overplanning is only an issue if you feel like you're going through the motions once you get there. If you've done it so many times in your head that it no longer has meaning in reality, you've overplanned. Those people freaking out because their plan isn't working out? Totally don't get why people call those guys overplanners. To me, they underplanned, because they didn't consider the fact that kids don't follow plans!