We haven't been to WDW 30 times, but over the past 10 years we've made 8 or 9 trips, including spending 50 days in the parks from June 2015 to June 2016, so we consider ourselves grizzled veterans. We do far, far less planning than most on this board (not saying it's better by any means, it's just what we do). We're very much wing it people. We don't stay on site, so I can't help you with the ADRs. However, we have completely stopped doing rope drop, we've found it's just not worth it for us. Again, not saying it's not worth it for anyone, just not for us. We'd rather get the extra sleep and/or have a nice breakfast at home than stand outside the gates for an hour. Just our opinion.
We definitely plan FP+. I think that's pretty important. Not a "must" by any means, because frankly we wind up changing probably 40% of all the FP+ we book...and frequently we change them on the fly while we're in the park that same day. Here's what we do, and it works for us....
About 45 days before our trip, my wife and I will grab a piece of 8x11 paper and list out all the days we're going to be at the parks. It's a very simple "calendar", just literally list each day of the week. We don't look at what park has EMH or anything like that, just list out the days. Then we decide what park we want to go to on a given day. There's no rhyme or reasoning behind it, except to try to give variation. We always start in MK, tradition for us. But after that, it's just rotational. We do get a "must do" list from the kids, and make sure we incorporate those rides, but that's a piece of cake. We'll list the park and then "AM" or "PM", as we rarely will spend morning to night in a park. We make sure that we have very few PM followed by AM days, so that we're not tiring ourselves out. We have one or two of those type days, but that's it. If it's an AM day in the park, the PM is listed as "freestyle". That simply means we'll decide what to do in the afternoon while we're eating lunch that day. And vice versa for PM days in the park. That whole process is done over a cup of coffee, so it takes maybe 30 minutes. Then we're done. When we hit the 30 day mark out, I spend 5 minutes on
MDE to book my FP+. That's it. No other planning at all.
When we get to WDW, we always start on that plan...MK first. But often on a long trip, by day 4 or 5, the kids will ask to change plans because they want to go to HS tomorrow when we had Epcot penciled in. OK, no sweat. Hop on MDE that night and try to change my FP+. If I can change it to things they really want, we swap. If not, we keep plans as is. Like I said, we probably change 40% of our plans less than 24 hours out.
The freestyle time is awesome. No pressure, no running around, nothing. If we're in the park in the AM as planned, like I mentioned our PM plans will be made while we're sitting and eating lunch. Usually goes like this.... "So, what do you want to do this afternoon? How about heading to the water park, then go home for dinner and go out for dessert? Great, sounds awesome!!". Sometimes we're tired and decide to go home and chill. Sometimes we don't. Just depends how we feel.
We wouldn't vacation at WDW any other way. We did run ourselves ragged when we first started visiting and felt like we had to spend every waking moment going from point A to point B. Not anymore. We never intentionally just waste time, but we're in no rush either and we very much wing it.
Hope this helps.