Don’t be a slave to a rigid bedtime hour or nap schedule. Once or twice a month, lighten up and enjoy holidays, family gatherings, or other special events. The well-rested child can easily tolerate infrequent missed naps or late bedtimes. But the sleep debt accumulated from the special event needs to be repaid! After the special event or illness, your child might be short on sleep and the strategy is a reset: A super-early bedtime for one night only and overnight, you might have to ignore protest crying. After a long holiday, especially if you cross multiple time zones, prepare yourself for one nasty re-entry night when you return home to fill up the now empty sleep tank.
I would consider a 5:30 reset once a month to be a completely normal variation. I have three kids, and one of them (my oldest) is like that. The other two make up the missed sleep from a cold or trip themselves. My oldest does not! About the only thing that gets him extra sleep is an earlier bedtime. We do travel a lot (we live at least five hours from all family) and have visitors a lot (one or the other at least once a month). If you are using the reset because of illness, travel, et cetera, you are just doing your job.
We do this when our son skips a nap or when his naps are way too short (thirty minutes) and he is getting overtired. Last week he went to bed at 5:15 p.m. and woke up at 6:30 the next morning, with two or three night feeds. We have noticed that this reset seems to work but with a delayed effect. His naps get longer the morning after the early bedtime, but they are out of sync (8:00 a.m., 11:00 a.m., 2:00 p.m.). It usually takes one more day of a 6:00 p.m. bedtime for him to be on the proper schedule (9:00 a.m., noon). Then we go back to our regular schedule, with bedtime between 6:00 and 7:00 p.m., depending on if he gets a third nap. No matter when bedtime is, he wakes up at 6:20 a.m. on the dot. Knowing he won’t wake up earlier (or later, for that matter) encourages us to put him to bed early for his sake.