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That's tough with the early mornings. I guess at that age, I would see the 5:30am feeding as a MOTN feeding and that his day actually doesn't start until the next feeding, so like 8:30am?

I generally believe in a 12 hour day, so if I count his day as having started at 8:30am, then an 8:30pm would be an appropriate bedtime. That would probably work really well for you if he's sleeping 9:30pm-6:30am, because then it would be more like 8:30pm-5:30am. He should be on his way to dropping down to 1 MOTN feed, so if you feed him once at 1am, that should get him through the night. Or, if you want to work on cutting that feeding, you can put him down at 8pm after a nice big feeding, then give him a dreamfeed at around 10:30pm or 11pm (i.e. your bedtime) and hopefully that top off will get him to the morning.

The bigger issue may be later on when the baby's a little older. Once they are STTN, I would probably want them to get at least 10 hours of unbroken sleep, so the bedtime would have to move to 7-730pm.

My son had issues (colic, reflux), so his bedtime didn't really regulate until 12 weeks, but WE mentally considered his bedtime to be 7:30pm (for purposes of keeping track of feedings and eat/play/sleep cycles). We started our day at 730am and just stuck to a 3 hour feeding schedule just so that we had some kind of game plan or template to work from because he basically just screamed and never slept for the first 3 months.

But once we got his colic and reflux meds figured out, he fell into a rhythm pretty quickly. We put him down to bed at 730pm, he got a dreamfeed around 10pm, and he would go until 730am. We worked on dropping the dreamfeed by moving it earlier and earlier in 30 minute increments, and once he was sleeping through until 730am with a 9pm dreamfeed, we dropped it completely (around 4.5 months?) and by 5 months we had an 11-12 hour a night sleeper, minus regressions.

DS is almost 19 months and he still has a 730pm bedtime.

- When did your LO's bedtime start to regulate? I don't remember! I didn't go back to work til she was 6 months and even then her bedtime has varied a lot depending on naps that day.
- Do you feel that your LO's bedtime regulated due to your efforts, or their natural development? Prob both. Not really our efforts but just because of the schedule we have to adhere to.

- What would be a good "bedtime" to shoot for? (As in, nurse, put down, he stays down) - Do you think that after about a week of these early wake-ups, he will start naturally going to bed earlier?
For an early wake up like that I would probably shoot for a 6:30 bedtime but obviously it is going to take a while to get there (and maybe he needs to be a bit older). I have to get my daughter up around 6 and I think we have finally settled on 6:30 as her ideal bedtime. This means that I almost always have to wake her up rather than her getting up naturally which I kind of need so that I can get ready!