He has started to engage in behavior that is clearly manipulative. He'll do things like ask for glasses of water at bed to prolong the bedtime ritual, tell us how much he loves us when he wants something that we're balking at giving him, or point out how he skinned his knee three hours earlier while asking us to give him a treat.
One time he even pretended to cry because I wouldn't interrupt my getting dressed for work to pick him up and carry him around the house. That incident involved him going into his bedroom crying, and closing the door behind him. He then opened the door, checked to make sure that I was looking, pouted, and closed the door again. When I walked away, he followed me out crying. When I asked if he was pretending to cry because he wanted me to pick him up, he admitted that he was, and immediately stopped crying.
He'll go through brief periods where he'll wake up in the middle of the night and cry until we come check on him, and tuck him back in. Then, between 30 and 60 minutes later, he'll do it again. This will happen 3-4 times a night, with explanations ranging from his blanket needing to be fixed, to bad dreams, to "I heard a noise". If I go in and tell him that he needs to stop waking us up, and that he needs to fix his own blankets, etc., he usually does, and the problem stops for a few weeks.
I know that at this age, there's a lot of "pushing of boundaries", to see how much he can get away with, but the deliberate manipulation troubles me.
Is this something I should be concerned with, and take special action to address?