I've had rotten luck the two times I used online check-in, but it was just that: rotten luck.
The first time, we were staying at the Contemporary. Arrived and there was no one in the regular check-in line, but two families ahead of us in the online check-in line. The family being checked in had like 7 people, all of whom seemed to be celebrating something, so the CM spent 15 minutes making pins and congratulating them, and they had approximately 8500 questions. As it turns out, we shouldn't have had to wait in line at all. We had been upgraded to a two bedroom suite on club level and the CM who was in the lobby waiting for us didn't realize we were there in line. Which, obviously, was awesome, but we still left thinking online check-in wasn't great.
Fast forward about a year and I decide to give it another go. That time we were staying at WL, one night only, no parks, no special requests, easy-peasy. Well, we had the delightful luck to check in right as someone in the back was printing out (no exaggeration) HUNDREDS of room keys. Not sure why or for whom, but she was using the key-printer the online check-in desk used. I stood there for easily 20 minutes while the CM waited to be able to print out my room keys.
Despite my crappy luck with it, I just did it again for our trip tomorrow
yay
. Third time's the charm, right? And, really, I could have crappy luck doing regular check-in, too. 
The first time, we were staying at the Contemporary. Arrived and there was no one in the regular check-in line, but two families ahead of us in the online check-in line. The family being checked in had like 7 people, all of whom seemed to be celebrating something, so the CM spent 15 minutes making pins and congratulating them, and they had approximately 8500 questions. As it turns out, we shouldn't have had to wait in line at all. We had been upgraded to a two bedroom suite on club level and the CM who was in the lobby waiting for us didn't realize we were there in line. Which, obviously, was awesome, but we still left thinking online check-in wasn't great.
Fast forward about a year and I decide to give it another go. That time we were staying at WL, one night only, no parks, no special requests, easy-peasy. Well, we had the delightful luck to check in right as someone in the back was printing out (no exaggeration) HUNDREDS of room keys. Not sure why or for whom, but she was using the key-printer the online check-in desk used. I stood there for easily 20 minutes while the CM waited to be able to print out my room keys.

Despite my crappy luck with it, I just did it again for our trip tomorrow


