The point of this thread is so that those of use who are insane can feel not so alone with our madness. 
Iāll start . . .
I keep checking historical flight arrival times 
for my flight so I can see if my plan for Arrival Day is likely to work out.
(This is one of the milder examples I could have chosen!)
I planned my trip about 500 days in advance and my family thought this alone was crazy.
I have run āsimulatedā days at the parks. I make a TP for a day with a similar CL as my intended day and optimize it, and then go through it in real time on the app using the reported wait times to see how accurate it is. I have even re-optimized on the fly to see if it makes a real difference (it usually doesnāt, unless something has gone wrong with the plan and it is going off track).
I am 30 days out. I have begun to look at weather projections hoping to find the one that will get closest to my dates. The real crazy part of this is that I do not know why I do this. I have no control over the weather and a forecast two weeks or a month away is really a work of fiction- but I do it anyway.
LOL you and I share that in common. Iāve already checked the weather from accuweather for our trip (which is still over 60 days away) and I know itās literally a shot in the dark but for some reason, I do it anyways 
I am 9 months out and I am reviewing and looking as if I am flying out tomorrow. I called my local book store and ask when the unofficial 2018 travel guide will be at there store because it comes out this month. I also simulated my ADR by putting in fake days I would be there.
you can start to see trends actually if youāre looking every dayā¦how are temps and rain %s changing week by weekā¦ not that crazy.
My next trip is Labor Day weekend- it will rain every day- I know that- I embrace my craziness.
I made a colour co-ordinated spreadsheet itinerary with notes on suggested snacks to look out for, travel times from the resort to the parks we were visiting, how we were going to use our dining credits, a budget sheet, wake up timesā¦ And our trip was made all the better for it! 
It was done in a fun way, not a militaristic one, and to make sure we had all of the bases covered so everyone could have the best experience possible.
I work in the live music touring business and next time we go I am going to make ātour booksā - like tour managers make for their bands when they go on tour and going to personalise them for each member of the party. I canāt WAIT!
This oneās probably a bit OCD
At the airport on arrival I count how many people are queuing to get through passport control.
Divide it by 3 (based on my estimate of average group size)
Then count how many staff are manning the desks.
Then time how long it takes on average for a group of 3 to get through.
Then do the maths in my head to estimate exactly what time we will get through.
And every five mins I go through the same process and adjust the prediction accordingly.
Sad I know.
Never get anywhere close. Iām always way too optimistic on how quick it will be.
Took us about 75mins to get through at sandford. And messed up our meal booking in universal.
My family think Iām far too regimental and plan too much.
I swear to God if I wasnāt they wouldnāt get half the enjoyment and rides and meals etc that they get!
They just donāt realise it!
Lol
I read all the trip advisor reviews on the restaurants we are visiting and tell them what they should be ordering based on reviews
I realise thatās bad!
But they ignore me anyway!
Since this appears to be a confessional: I have a file for each of our trips. In those files is EVERY (and I do mean EVERY) piece of paper that pertains to that trip. Printed emails, fuel receipts, vet papers (dogs go to Disney kennels), printed touring plans, park maps, any special park printing (Food & Wine passports etc.) and EVERY blessed receipt from the time we leave the house to the time return. Each is its own scrapbook. When planning upcoming trips is a perfect reference point. At least thatās my justification. No, I will not Let It Go. . .
My kids started counting down at 596. Do thought I was nuts buying the UG!
I did this last Christmas 
And then Pandora happened and Iāve got no clue how is going to impact my plans!
Did this also! My kids LOVE it. Normally I get thermal bound books made, but this time I am doing binders.
Last holiday our books included turn by turn driving instructionsā¦ From the pointy bit of Aus to the very bottom. And public toilet locations for every town we passed through.
My family wouldnāt ever get around to booking the holiday in the first place if I left it up to DH
I might have packed our carry on bags back in Novemberā¦ For our trip this Christmas.
I do something similar!
I love showing the āNon Plannersā my Tour Plans. Everything planned to the minute. I feel bad for the people that just wing-it.
The fact that this website exists had been enough to put my SIL off going to wdw ever. And sheās the super organized got it all together type that makes normal humans look incompetent at life!