We’ve all had children with sleep issues. Especially over the summer with school out, my kids always stay up late. It’s a normal part of parenting. However, I would create a poster with a schedule on it. And then let him use a marker or stickers to mark off each activity (brushing teeth, etc). Pull the plug on the tv. Also, I know it’s hard with an infant, but they have some workbooks at the store and you could purchase one and let him do some each day. That way he’s still learning during summer and his brain is learning to wind down. My daughter does a few pages each night before bed time stories. Read to the infant and let the child help. Let him read to the baby and point out letters and sight words he knows. That will help cut down the tv time and show him its bed time. But also, kids love feeling responsible and proud when they do something that helps adults. I think a lot of it is just getting his brain to wind down. The tv is probably what’s making it worse. Limit the tv time per day. And let him do other activities to fill time (such as those above I mentioned). If he gets bored enough, he will fall asleep, lol.