G.B.
You need to go back to putting him in the crib at his sleeping time and holding your ground.
If you being in the dominant position and your child in the submissive position is considered by you a "punishment situation", your going to have a hard, long run of parenthood. You should re-think this.
The natural order of things is that you get to call the shots being that you are the mature one and know what is best for your child. You have been put in an authority position over that child by God himself. God did that because he knows the Child's brain isn't capable of making sound judgement calls! If you know that a nap is what's best for the child, then hold him to what he needs to do. It has nothing to do with punishment, it has to do with love. Do you love him enough to do what is best for him, what will be healthy for him, what will help him in the long run, even if he might not "like" it or "feel" like it at the moment? If you design your parenting on making him "feel good", you are missing the idea of what a parent was designed to be and you are setting your self and your child up for failure.
I GUARANTEE you that the more you hold your ground, the more respect your child will have for you.
Don't think you will be able to tighten anything up as they get older, either. It actually works the other way around. Start out with a tight belt, and loosen it up as they grow up and have shown that they have matured enough to be ready for more "responsibility" and decision making.
God Bless,
Gail