5. Spontaneous character meet and greets 

There are quite a few characters who turn up as expected, right where you want them to be.  Winnie the Pooh will always be available for dinner at the Crystal Palace, and you’ll never miss out on Ariel if you visit her Grotto.  But exactly when and where will Peter Pan happen to turn up?  Should you hang out and wait for Gaston at his tavern?  When will he be back?  Will there be a long line?  So many of the most magical character encounters occur, not because you’ve waited in the right spot for the right moment, but because you just happened to be in the right place at the right time.

6. Meeting fellow visitors who happen to click (or NOT) with your group

You walk out onto your balcony, and right next to is a family that’s just terrific.  They’re fun, interesting, and (most importantly) they’re quiet, considerate hotel guests.  You decide to get together for a delightful meal, and it turns out you have a lot in common.  You trade contact info, and meet up again multiple times over the years. 

OR…  you happen to be lodging next to the loudest most obnoxious group of people you’ve ever met…  you’re seated at a pricey Signature Restaurant next to the Toddler From Hell (and there are no other tables available)…  you spend an hour in line at Peter Pan with the world’s most unpleasant family, just trying to keep their kids from pushing your kids into starting World War 3. It'd be nice if all Walt Disney World guests were nice and pleasant, but the reality is you'll probably meet some visitors you'd rather not run into again. 

7. Technology works against you

It's no secret that MyMagic+ isn't a perfect system, and unfortunately, outages have been known to occur. And although Cast Members are usually as accomodating as possible in these situations, a MyMagic+ outage, a disappearing FastPass+ reservation or even a non-functional Magic Band are all things that can derail an otherwise amazing Walt Disney World vacation. 

8. Travel plans go awry

First, there’s the arrival in Orlando.  And as we all know, air travel is a crap shoot.  Sometimes it’s smooth as glass.  Sometimes it’s …  not.  You can lose half a day of Disney fun because of rotten weather in Texas – or arrive ten minutes early, fresh as a daisy.

Then, there’s the Magical Express.  Is it ready to go?  Or will there be an hour-long wait as your driver copes with difficult passengers, discovers that someone’s luggage is still on the way, or waits for the rain to calm down a bit before hitting the road?

Perhaps most luck-related of all is the transportation at Disney World itself.  Yes, you can use an app to get a gist of what’s coming and what’s not.  But how long will the bus queue be?  Will your party fit on the bus?  Will there be room for all your strollers?  How long will the wait really be for the monorail, which appears to have suddenly lost power somewhere on the line?  How about that boat, which is evidently waiting for someone’s lost party member to arrive?