Some people need to be in control and try to plan every detail in their vacation. Which is understandable. I plan my trips months, even over ayear in advance to try to get the best advice up to date. For me, I plan my trip on several small but important aspects:
*When is the cheapest time to go to WDW?
*Will it be crowded during this time of year?
*Will the weather be tolerable during this time of year?
*What rides should we go first?
*How much money are we willing to spend on expenses? (Food, Beverages, Suvineers, etc.)
For us, I planned my trip in November for several reason: hate people/crowds, weather, and costs. After saving and careful planning we had $700 to our name for expeneses for our trip. Doesn't seem like a lot of money for a week trip for two but we did cut expenses (bought snacks and bottled water so we rarely had to spend money on breakfest and we also ate dinner early so we saved an extra $20 per person on dinner.) And the only "Danner Tanner Clipbook of Fun" thing we did was hit the first three rides in the morning and afterwards it we did whatever we felt like.
It all depends on the person, how many people are going, and age obviously. I'm probably rambling like crazy but I believe you can plan your trip extremely well without going "crazy" or "neo-nazi." My DH at first thought that I was going to be " retentive" on planning our trip but after the first day of our trip he was so happy that I did the research and planned everything well and so laid back that if we didn't plan our trip and do our research we would have been miserable and probably broke by the third day.
Hoped this helped you a bit.