My brother and his family came with us to WDW for their first trip last November. They had absolutely no clue. Every time I'd check in with them about stuff like ADRs, accommodations, FP+, he was so incredulous that we needed to decide and plan these things so far out, especially since we were a party of 8. He even got annoyed with me at one point because he felt I was going overboard with the planning...probably a fair assessment, but I was just trying to make the trip magical for his kids (who had never been before) and mine. Going during Free Dining in November took planning to a whole new level because so few of the things they wanted to do were available 180 days out. I was online every day from Day 180 until the day we left trying to plan things, pick up ADRs that people dropped, and then later booking Fast passes one at a time and then eventually migrating them over to be within the time window so we could all ride together. It honestly was a soul sucking exercise.
But that was the "invisible" side of the planning. Nobody knew how much time I spent except me.
Then there was the in-park planning that had to take place when plans needed to get rearranged (constantly) which necessitated an inordinate amount of time on
MDE every day. It was so hard to manage a large group, even building in a fair amount of time to let people go off on their own. The park crowds were like an 8/9 and so if we missed our ADR or FP+ windows, we weren't getting new reservations without a significant amount of work, or at all.
I was going to take my daughter for a short trip at the end of August, and she told me not to bother...that I spent too much time on my phone planning and that had made it much less fun than when we first started going together in 2009 before FP+. I felt horrible that I had let planning get in the way of the fun (at least from my daughter's perspective). So there is a definite downside to the planning as well. Because I hate crowds and standing in line so much, I probably overplanned the amount we'd have to experience either of these. Maybe we need to go with the flow a little more, with a little less planning. If the line is too long for a ride we can decide to skip it that trip, or if crowds are too great, we can splurge on hoppers and go somewhere else or just go back to the hotel and relax. The point is to have fun, and it appears the overplanning took the fun away for both of us. Lesson learned the hard way.