I'm sorry you are having a rough time getting your little guy to nap My DS isn't the world's best napper either. I figure that if he STTN that's good enough for me...but then again, I'm at work 3 1/2 days a week so I'm not the one who has to entertain him on those days when he won't nap...but I digress...I know this might not be the most popular approach (no flaming please!), but have you tried letting him cry for a little while? Some people say you have to wait until 6 mo to really let them CIO, but we tried this with DS when he was around your son's age and it really worked (ok, so not for naps, but at night it worked!). Good luck!