I don't think I regretted my trip last year, but it wasn't quite as great as I expected. That was all my fault though, sorta. My parents, brother, and I took my 6 year old nephew, and I pretty much took care of everything. Like some do here, I had a good plan in place. Well, pretty much nothing from my plan worked out. Yeah, the major parts (certain parks certain days, FP+, ADR's) were fine, but it was the "smaller" stuff.
I had planned to get up and get going early every morning, but my brother and nephew never felt like getting up early. I get it, we are on vacation, but to make the most out of the day we needed to get to the parks right around opening. We went at a slow time, but still wanted to take advantage of the earlier mornings. Not that we were that late, but we would get to the parks an hour or two after they opened.
I also had planned to take a break every day, but with the later entrance it wasn't worth it. By the time we did what we wanted it was 4 or later, so if we went back, we wouldn't have much time to make it back to the parks (January so earlier hours). So not only did we not get a break, but by the mid/end of the day we were all cranky. I know some people can be in the parks all day, but we aren't cut out for it. 6/7 hours at a time is enough for us.
I also wished we would've gotten hoppers. We felt like we HAD to stay and enjoy the parks because the next day we couldn't come back.
The weather also didn't cooperate. We had no rain, but it was too cold to swim most the week. That really upset my nephew as he seemed more concerned about swimming than going to the parks at some points. I spent thousands of dollars on a vacation and he wants to swim?
There were some other annoyances here and there, but not keeping with the "plan" was the worst for me. I'm a planner. And while it didn't have to be to the T, we were so far off it was upsetting me.
We've decided to go back next May. I'm planning hotel, FP+, a few ADRS, but other than that there is no plan. Well, I have my own idea of what I'll want to do, but I'm not planning so much this time. We've discussed that we're getting hoppers this time, and everyone is pretty free to do as they please. If someone wants to sleep in, they can catch up (well, not the nephew by himself of course haha). If my nephew wants to swim all day, hopefully someone wants to relax that day and they can stay back with him. If someone wants to go back early, go for it. If no one else wants to go do something, we can do it ourselves (although at least one other person will want to do it too I'm sure).
I think I wanted my plan to work, and we felt we HAD to do everything as a family. While it's nice to be together and it would be more fun, to a certain extent we're not trying to please each other next time, and I HOPE that'll make for a more enjoyable experience.