Loved reading your report…I think in reality you were rather positive in spite of some issues that a lot of people could let ruin a trip…you sound like a great mom!
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I think it depends on whether they normally nap on the go, if they only ever nap in their cot in can be hard to create new habits.
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Honestly, I think it was eventually just pure exhaustion that made him sleep during the day. Sometimes he would fall asleep on a dark ride (I held him during Spaceship Earth and he fell asleep in my arms which was so cuddly and nice 
) and we’d be able to put him in the stroller and he’d stay asleep. And some other times he would fall asleep for only 15 minutes so it was kind of luck of the draw! I will say, we are very lucky and he is a pretty adaptable baby. If we had tried to take my daughter on vacation that young, I don’t think she would have been as happy during the day without her naps. Getting home was another transition, though. He had to get used to naps and sleeping in his crib again (he shared a bed with DH because he freaked out when we tried to put him in a pack and play in the hotel room). But after a few days, he got used to his old routine
I think for some people this works, and that’s fine…but it’s not my vacationing style. Although there were a couple of moments that I got caught up in the rush-rush of things. I think I left out a few things because I blocked them out…like when we were trying to make the Frozen Sing-Along show. I told DD to wait with daddy and I was going to park the stroller, but neither of them heard me apparently. So I park the stroller, then hurry back to the group and I’m like “Where’s Samantha???” She was back by the stroller, crying because she didn’t know where I was. She is still talking about this. The whole thing lasted probably 15 seconds but it was the scariest 15 seconds of the trip 
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AWWW! 
Thanks!
We’ve had a few “bad parent” moments related to losing our kids (which I won’t go into here). But, as a result, one of the things we now do is tell our kids that if they EVER get separated from us accidentally, to find one of the park employees and let them know you are lost. We point out what they look like, so they can be sure.
Of course, by doing such a thing, it has guaranteed it has never been necessary. But it is nice for them to know in case a separation DOES happen.
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We did the same… talked about who they should find to help them. I also wrote my phone number on their Magic Bands and said that they could ask ANYONE (at Disney) to call us.
Like you, we’ve been fortunate to never need it… at Disney.
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