The planning never ends for me. Even when I arrive, I am tweaking the plans. You never know if there may be a better FPP drop, a different meal reservation, a new snack to try, a new dessert party to attend.
I say this is me planning on the fly and being flexible while circumstances change throughout the parks.
Even after the trip is over I am tweaking the plans, reviewing what changed from my initial plans and how I can get back soon to tweak the plans a little more.
Some say this is OCD.
and then its time to start planning a new one!
Or do like me, and plan two at the same time! 
I have 3 trips in current stages of planning 
I’m already outlining 3 trips in 2022. I’m sure by the end of the week I’ll have fully detailed plans for each, with contingencies for what might be open and what my kids might be into by then. It really is a sickness…
Y’all are all on a different level than me! I am on the level where I try to convince my husband this is a worthwhile way to spend our vacation time.
I dipped his toes in with DLR a couple of years ago and I had to trick him by calling it a trip for baseball games and then, oh, look how close we are to Disney!
Bahaha! It totally is a sickness. Every time we come home from the world I’m like “what did I used to do with my time???”
Thanks! Can’t take credit though…I googled Disney puns and this was on the first page of images. I do love tacos, but I’m more of an Ariel in real life.
On second thought, I do relate quite a bit to Belle…small town girl, loves to read, would do anything for family.
thought this was just me 
this was totally me for my first trip! I completely approve but have a couple of warnings that are 100% from my first, over planned trip:
make sure your DH does not think that because you spent so much time on the plan, he needs to be the enforcer and make sure everyone follows it
with little ones everything goes sideways. Your planning will let you recover to do the top priority things. But if someone finds the moat ducks magical, let them experience the magic of the ducks in the moat!
remember you cannot do it all. WDW is like an onion, there are layers and layers to peel and you can’t get to all of it. That is why people keep coming back! Pick a couple of rides, one meal and snack, and maybe one or two cool things you have heard about here as your “goals for the day”. Then everything else is extra! Based on some of Len’s data, 7-8 “experinces” in a day should make everyone feel satisfied. Make that your goal!
I am going on year 6 of Disney planning being my stress release. It isn’t cheap, but it a lot healthier than other alternatives! If, however, it adds to your stress, that is when you should step back.
Good luck!
I totally have an Angel’s game planned for my DLR trip in June. This is how you keep coming back!
I have a binder with ALLLL the plans since we are driving multiple days to get there, and I have a binder strictly for Final TP days. My newer family members think I’m crazy and this will be a stressful, hectic trip. My 2 girls, have been once before and know the planning worked out perfect, they keep telling the newbies to “hang-on, she’s got this.” 
We had a really good time! I have been to DLR several times, but it was a first trip for him and our daughter and the baseball game was a nice way to break things up.
I considered doing a day trip to Tampa, but the logistics of 3 car seats and a rental car for 7 made it not worth it.
This is all very hard to predict. I took my 2 kids when they were 3.5 and 13 months and then again at 4.5 and 23 months. My suggestion is to book a mix of the tougher FPs for the “bigger rides” and somewhat tough FP for attractions that everyone can enjoy. For MK for example, I recommenced 7DMT for your 4 y/o and Peter Pan for everyone. For the 3rd FP, consider BTMRR, Meet Mickey, Jungle Cruise or Meet Cinderella.
You will likely need to make many adjustments on the fly. And this is where all your planning comes in … the more you plan and plan and plan, the easier it will be for you to make smart adjustments as you go.
Can’t convince your wife to shoot for 2020 or 2021? I had a a 4 year WDW break (went in '14 and '18 but no trip in '15, '16 or '17 due to pregnancies/babies), and the withdrawal is real!
When you’re done that day. Then you change over to touring report mode. But don’t let that stop you from fine tuning for the next day.
Things come up. It’s important to be on top of them in case you need to make changes. I finalize my TPs the night before (bring a printer with me) and print them off. Then, in the morning before we leave, I do a double check to make sure there weren’t any changes to timings or anything and adjust accordingly.
What a great idea!!
I’ve had 3 trips and it depended on what I got during ADRs and FP. The 2nd trip was the golden trip for planning b/c I got everything we wanted and was able to stop planning at 60 days. Not so with 1st trip when I started too late and chased ADRs until the day of, or our most recent 3rd trip when I just simply never got one of the FP or desired ADR time (which didn’t turn out to matter anyway). Could I have stopped at any time? Yes, but I like chasing ADR and FP. I kind of miss it now! Also, the 3rd time we had some big challenges I didn’t expect, like child developing foot problem and relatives showing up unexpectedly at WDW that I needed to go see. So I actually kept on adjusting things until the very end…which I found exhausting. But those were things I could not have foreseen. I also cancelled several things that I had booked as a “this would be nice but I might not have time” sort of plan. It was ok to cancel but still kind of hurt. These were things like Mermaid School at AOA for my daughter, and it was too cold to swim at 8 am I thought. Anyway, if you feel like it’s time to stop planning then feel free to give yourself the space to do so. But if you like it then carry on.