I started planning our last trip a full year in advance, as soon as I got the approval from my wife on the dates she wanted to go.
I told her I would plan:
Every detail involved in the actual travel to and from WDW (travel to and from airport, flights, etc)
Every detail involved in the lodging (which resort, room view, length of stay, etc)
Every detail involved in food (dining plan, where we would eat table service meals and when, rough estimate of where and when to eat counter service, and winging it on snacks)
Every detail involved in attending the parks (tickets, ticket options, park transportation, which park on which day, etc)
So I hopped on the disney site and customized a vacation package. (Ok, customized a million of em, until I found the one I thought would be best. Yeah, I know, cheating, and not cheap, but hey, I didn't have a worry in the world. Everything was taken care of and paid for in advance, with the exception of gifts and keepsake type spending. The only thing I carried around the park was my DL and my room key. (which had a CC tied to it).
But I also told her that once we were in the parks, I was winging it.
That we would pick a direction and go. We started on morning EMH, and if it got too busy, we would hop some place else, as long as we ended up in the park where dinner was scheduled.
It worked out pretty good IMO.
We rode everything we wanted, multiple times. If it was packed when we got there, we returned when that park had morning EMH and rode it first thing that day. We had some attractions that were 2 hour waits when we got there, so we skipped it and the next day at EMH it was walk on, so we rode it over and over.