When to sleep train?

I am having such a difficult time at bedtime with my baby and I feel like I have tried EVERYTHING I could possibly think of. He’s 5 months old. We have a solid bedtime routine (bottle, bath, lotion, read/singing, sleep sack, bed). He’s not a very good napper but he’s usually awake 2.5-3 hours before bed and naps about 3-4 times a day. I’ve tried doing 2 hours, 2.5 and 3 before bed with all the same results. I’ve tried earlier and later bedtimes, same thing. So he goes to bed at 730/8 which seems to be the best time.

The PROBLEM is he wakes up 1 hour after bedtime like clockwork. Then he’s up every 20-30 mins until 9/10pm then stays asleep until about 1am and again at 530. I totally understand night wakings are normal at his age but it’s the bedtime that’s been issue. The room is dark, cool with white noise. He definitely does not sleep too much during the day.

He doesn’t take a pacifier at all either.