Hi all, I am new here

My little one is almost 5 months old and with the 4 hr easy is doing great. He falls asleep on his own in his crib at nap time quickly with no fuss. Bed time usually is also easy now, but he sometimes wakes about 45 minutes later and is very upset for often 1 hr or more! My husband leaves for work at 5 am and sometimes wakes him accidentally also. My problem is that PU/PD isn't working. It did at first but now he gets hysterical and screams at the top of his lungs. Whay is he waking in the evening do you think? and any idea's about dealing with it? Here is my schedule...
7 am wake him and feed
7:30 activity
8:30 start wind down
9 sleep 1.5 - 2 hrs
11 feed
12-start wind down-he gets very sleepy and sometimes naps early
12-1 goes to sleep sometime in this window, usually 45 minutes.
2 activity
2:30- 3 feed
3:30 activity
5 feed
5:15-6 cat nap
6:30 bath
7 feed and bed
10 dream feed- was 11 but have moved it to 10 starting yesterday.
So, he has a short activity time after 11 am feed before nap and I am still cluster feeding plus dream feed. His 2nd nap is short also.
When I do PU/PD I soothe in crib as much as possible, hold a short time until he stops crying and put down immediatly. I put my hand on his chest instead of his back. He arches his back and screams while holding at first and in his crib. I put down if he does while I am holding him. He will close his eyes and mantra cry, suck thumb and turn away and I think he is going to sleep then it starts all over again. The cycle repeats for up to 2 hrs with no end. Just when I think it is over it starts again!
He self soothes so well and goes to sleep on his own during the day that I have tried not going in to him at night. He falls asleep within 20 minutes usually, but I feel like a bad mom! What am I doing wrong?