So sorry your trip had so many bumps in the road. It certainly sounds like you made the best of it. T is very lucky that you put so much thought and planning into your trip. It is sooooo hard to find that balance between packing in too much and being stressed and being pleasantly busy. I think we've all been there. During our first trip to Disney I should have listened to my son when he said he was hot and just wanted to leave AK. I pushed and said we should just go get ice cream and recharge and we'd be ready for our next adventure (funny how now I can't even tell you what I was so worried about missing). As you can imagine, about 20 minutes later there was a meltdown and we had to cut our losses and head back to the hotel. It took hours for all of us to recover from our misery! As you say, we learn from our mistakes and move on. On our next Disney trip when there was a heat index of 105 on our AK day and our son & daughter both said they were too hot and wanted to go back to the hotel, I started to try to convince them to stay just a little while longer. Luckily a little voice in my head, and then the more insistent rational voice of my husband, reminded me of what happened last time. I forced a happy face and we left and went for a swim.
Thanks for sharing your experiences. It's nice to know we over planners are not alone!