I'm a hardcore planner and have always been. We usually go with the MIL. For our first
Disneyland trip with the kids, wife didn't want to plan anything. Just go with the flow. During the trip, I said "we could be doing this or doing that" or "should we book a fastpass for this or that in anticipation of what's going on?" I made it clear that I wanted one evening just the two of us while MIL watched the kids. When it came to that point, MIL said no, I'm tagging along with you. So upset. Forgive me for expressing my wants before the trip, trying to set expectations so that there are no arguments. I should have been clearer or gotten express agreement. Lesson learned.
For our very first WDW trip, I planned every second. Wife and MIL didn't like it. Said it was too stressful. However, on one particular day that trip, I had no plan. When wife and MIL asked what we were doing, I said I had no plan. I said it's your day, you can plan what you want. They didn't know what to do, because, well, they didn't do any research. The resentment was overwhelming that day. How dare I put some of the responsibility on others as to what we do that day.
Over the years, it's worked out though. I've gotten very very good at planning for the unplanned. I think that's where my (and a good planner in general) strengths lie. It's not, can you get everything done, but can you get your plan in when something goes wrong or needs to change? I always build in break time, slower walking speed, rides breaking down, transportation issues, weather into my plans. I scenario build and always have backup plans. What happens when someone is tired, or sick, or doesn't want to do something? How married am I to this restaurant reservation, or can I let it go because we just are not feeling it? If we have energy, we can do X, Y, & Z. If we don't have energy, we'll just settle for Z. I also make sure I get 100% agreement on everything? Do we all agree to get to the bus stop by 7am? Do we agree to have MIL watch the kids for these rides? Etc. If I don't get agreement, I have to be prepared to make decisions on the fly and communicate the consequences of our decisions.
It was dicey the first couple of trips, but we all have a good system now.