Our ODD would NOT nap in the stroller and so EVERY trip we would go back to the hotel for a midday break. Since our first trip with her was offsite at a condo near Sea World (!!), everything since then has seemed easy! Our schedule usually has been "as close to RD as possible or PPO ADR" to noon-ish, then back to hotel for lunch + nap, then back to parks for dinner (5pm ADR) and maybe a ride or fireworks. Even as ODD has stopped napping at home, she LOVES fireworks, so lately she's not had a problem napping at WDW in the afternoon with the incentive of getting to stay up late to watch fireworks. (Sometimes the fireworks were from our room)
Last 2 trips, YDD was a baby and napped in the carrier or stroller. Next week we will try the midday break as well, and see how that goes now that YDD is almost 2. It could be a total fail. But she seems able to sleep almost anywhere when she's tired, so I'm not as worried as long as we have a stroller.
The midday break works well for us, but that's largely because we stay in resorts that are v. close to the parks, and because our kids would be horrifically cranky without a break. Also, I hate the heat, so it's a nice calming break. And this way we can stay out later than no break, and still have our kids somewhat well-behaved. Also, our kids are super early risers no matter when they went to bed, so while they are still young, we'll front load our park time to the mornings and have calmer evenings. When they're older we may use the midday break as a pool break or still a nap (I remember napping with my parents even when I was older), and then stay out much later at night.