E.S.
You know, every kid is different. It sounds like your little one falls asleep easily and quickly for naptimes alone in his crib...but it is more difficult at night to co-sleep even though you know he is super tired. Maybe he is a solo sleeper. It sounds like you and your husband enjoy the co-sleeping, which is fine...but if your little guy isn't getting the sleep he needs, maybe he would do better solo.
Listen to cues from your children. If you are good with the co-sleeping..and that is what they are responding positively to...then go for it. But if they want to sleep alone...or sleep better alone...then follow that as well.
As parents, our job is to do what is BEST for our children even if it isn't exactly what we want.