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Have you tried putting him down a bit later? It might just be me but 5:30 seems really early to me. My son went down around 7 at that age. We also did a tank up feed of pumped milk (a 6 oz bottle- the biggest bottle all day). Might be worth a try.

I don't know that I have any advice. My DS1 was like this. We constantly struggled with sleep,
and CIO didn't work because he would literally cry all night. We had a really rough first year, and a fairly rough second year. Nothing anyone told us really worked, or if it did in the short term, he'd go right back to sleeping crappy again soon. We spent quite a bit of money on sleep consultants, books, etc. In the end none of it was super helpful. Our kid just didn't fit the mold. I hope you do get some good and helpful advice, but also know that all kids are different. What worked for one person may not work for yours and of course vice versa.

Maybe you could try to gradually get him to stay up a bit later (like 15 minutes every few days). To keep him up you could do bath time at night before that last feed. Just a thought. Good luck, mama. That's tough!

@AprilFool: where is he going down at at 5?

The biggest things that have helped us with sleep are get them out of our room ( and we're staying with our parents at the moment so this hasn't been easy) but I would do this by any means possible - large bathroom, large closet, etc and have dad so bedtime. Then the kids seemed not to associate it with me and feeding so closely.

@AprilFool: I haven't read all of the respsonses so sorry if this is repetitive!
I am a HUGE proponent of early bedtime but I would say that 5:30 is pretty early! I also completely understand and agree with the short wake time when they are that age. And actually for us 2 hours was still too long of wake time at that age.
For the 2nd half of the day, my suggestion would be this based on the sample schedule you gave in one of your responses and our experience. And keep in mind you need to give anything you try 2 weeks of consistent effort before you can say it doesn't work - that's basic sleep consultant advice.

1:15-3:30 nap
5:15 - 6pm nap (gently wake at 6pm)
6:15pm start bedtime routine (everything from final feeding to bath to story - whatever your routine is. And if you don't have one, START!)
7pm should be in bed with lights out.

I've always found that taking the catnap around 5pm helped avoid any kind of witching hour and gave us a very pleasant bedtime routine experience. And having a short wake time between that cat nap and bedtime never mattered. It was still the end of the day and he was still plenty ready for bed. A 45 min nap gets you some extra time in the evening but it's not restorative enough to stay up for another 2 hours. It always worked perfectly for us.

Also, you have my sympathies. The 4 month regression was by far the hardest one on us! My overall advice is to stay mostly consistent and it will pass! But making some minor, favorable adjustments to help them through it is a good thing.

@AprilFool: yay! Hope the sleep just gets better and better!

Reviving this thread bc I need help too. My 8.5 month old has been going through this since the week of thanksgiving. We've tried everything including cio and nothing is working. She has 2 teeth, is not sick. Same bedtime routine. She refuses dad at every MOTN waking, I don't know what to do anymore, I am so tired.