Have you thought about the possibility that light in the room might be a problem? I was wondering what the difference is between naptime and bedtime. A couple of my kids are VERY sensitive to light. My daughter's room has a room darkening blind over the window, PLUS black out drapes. Even then, if the crack in the middle of the drapes comes barely open, she will wake up too early. They were never able to take naps at other places where we couldn't control the light. In addition, we use sound machines to block noise. Maybe he's just more sensitive to these environmental factors than his brother. Another thought might be that you are not winding down enough at naptime. It sounds like you have a long routine to prepare him for bed at night. Maybe make him do a half-hour of quiet time before nap, where he has to only sit on the couch and look at books, with no TV, no running around. Perhaps put on some soft music. I also have had great success with the Ferber method, so you might have to try going longer than the 10-15 mins. If you are willing to get him out of the crib that soon, he is willing to stick it out until you do. I know it's very difficult to have a child that won't nap without you--I've been there with one of mine who was constantly sick. But hang in there---this too shall pass! Good luck!