I booked a trip for April 11-16 early March and booked my park passes then.
On the other side of your coin, we have been going since 82 and have rarely planned anything. I've been known to book a hotel 2 weeks before going back in the days when you could buy length of stay tickets. We have always had park hoppers. We used to just go to CS in the morning and ask them to find us somewhere to eat that night, since we had hoppers the park didn't matter. If it was slow enough the CMs would make a game out of it and compete with each other to find us something. When paper FPs came out, sometimes we would get them and sometimes we wouldn't. More often than not we would get them and give them to someone else when we were leaving the park. We just hopped to another park if the park we were in was too busy. When the new FPs came into play, we might book one while standing in line for a ride but it would only be 30 min. out and never more than one at a time. Now, we check
MDE while walking around and book an ADR for that night for whatever is available. I have my hotel and park reservations booked for next week and that's it. No ADRs, I'll eat a lot of meals at the F&G booths and will wing it the rest of the time. I've been looking at MDE every once in a while and have always been able to find something for the night I was looking. Trick is to have PHs, and not care about time and enjoy trying new things.