Is it weird that my 2.5 still wakes up during the night?

My son has never been a great sleeper… as a baby he didn’t sleep well at all and we eventually resorted to sleep training. We finally got him sleeping for like 8 hours straight and that was fine with me (this was around 6-7 months old). He would go to sleep at 7-8pm and wake up around 4-5am and I would feed him a bottle and get him back to sleep until 6-7am.

Well now he’s 2 and a half and he STILL wakes up once a night most of the time. He goes through phases where he’ll sleep right through the night (10-11 hours), but I’d say on average he wakes up 50% of the time. Right now we’re going through a phase where he wakes up crying 2-3 times per night and I’m going crazy… we have a new baby due in 8 weeks and I’m feeling desperate to find a way to get him to sleep through the night regularly. I just don’t know what I’m doing wrong! He doesn’t nap for too long during the days (daycare caps it at 2 hours) and we’ve already been moving his bedtime later and later because he’s never tired and he never wants to go to sleep at 7pm. We’ve started doing his bedtime routine around 7:30 but he doesn’t usually fall asleep until 9pm these days (he just fights it and we spend around 1.5 hours each night going in and out of his room rubbing his back and telling him it’s time to sleep, while he cries and calls for us to “come back” and “stay here”).

We still give him milk when he wakes up in the night and I’m thinking that maybe we need to cut that out cold turkey… any shared experiences and advice from other mamas who have been through this would be extremely helpful! ❤️