Ok I need thoughts and ideas here! My little guy just turned 6 months old yesterday and we are having night time sleep problems. Naps are fantastic. We cuddle for a little bit, put him in his zipadee zip, read a book, put him in his crib, walk out, and he is always asleep within 10 minutes with little to no crying. Bed time is a different story though

Our bedtime routine -
7 - Wakes up from last nap, gets diaper change
7:15 - Eats cereal and fruit then digests for a few minutes
7:40 - Nurses (we are just starting to move this up from right before we put him down)
8:15 - Bath time
8:45 - Book and some cuddles
9 - In his crib

Once he is in his crib we say goodnight and leave. He will usually babble for 5-10 minutes but instead of falling asleep like he does at nap time, he goes full on ragey baby. Last night he cried and screamed for over an hour before I gave in and brought him down to our room to sleep in his rock n play. We have tried letting him cry for 10-15 minutes straight, we have tried going in and comforting him with our voice only, we have tried going in and comforting him by picking him up and then putting him down when calm, we have tried rocking him, we have tried shushing and patting on the arm (which always used to work). I am out of ideas. I feel like he is overly tired but I don't know how to get him to sleep earlier. Our typical sleep schedule looks like this -

9 am - wake up (we are trying to move this up slowly)
11 am - Nap #1
12:30 pm - wake up
2:30 pm - Nap #2
4 pm - wake up
6 pm - Nap #3
6:30 - 7 pm - wake up
9 pm bedtime

I am open to any and all suggestions