I think there is a fine line between planning and overplanning, at least when it comes to me and my daughter. I should mention that I had the Deluxe Dining Plan each trip.
My first trip in 2010 was largely this way. I only made 3 ADRs for the trip (2 weeks at CBR). Those being an early dinner at Royal Table on the first day, Dinner at Akershus 7 days in, and Royal Table on the last day.
We had a blast, and while I couldn't get in everywhere I wanted to try, like Le Cellier (I checked almost every day and whenever I walked past the seating podium in case there had been a cancellation or missed reservation). But, we got into most places I without a hitch.
In 2011, I did another 2 weeks at CBR, and booked a few more ADRs (I was determined to do Le Cellier this time). Again, Royal Table on the first and last days, BBB on the last night, Brown Derby with Illuminations Package. I expected when we arrived we would have a similar experience, but I don't know if it was due to the Free Dining Package push in the earlier part of that year, or what, but my daughter and I had lots of trouble getting into Table Service restaurants...even if we were willing to wait for a while.
So, fast forward another year to this past trip in 2012, and I was a planning fanatic. This was for two reasons. Each of the previous trips, I'd left with quite a few meal credits left over, and so I wanted to be more efficient. The second was my experience having trouble getting into Table Service in 2011. So, I booked 2 ADRs a day, and sometimes more (but, normally Lunch and Dinner). I was excited going into the trip with my now 7 year old, but for us, this planning measure on my part was a huge mistake.
We like to just take the parks as we go, and at a whim. All this planning had railroaded us into going to certain parks on certain days, regardless of weather or our respective moods and interests, or forced us to park hop (which we do normally anyway, so it's not the hopping that's bad, it's that we are now FORCED to by the ADR). This meant that, while we ate a lot of wonderful food this past trip, we missed a lot of our normal things.
Looking forward to my trip next year, I think I'm going to dial it back some. There still are things that pretty much require an ADR (especially since I go in mid-late August), so I will still have them...
I still haven't found that sweet spot, and maybe I never will, but overly regimented planning really sapped something out of our last trip, so I'm not going that route again.