More hugs... I agree with Koe. WIWO just wasn't an option when my daughter protested sleep. I tried it and it just did not work. The way I would approach it is say to him and yourself, 'it doesn't matter if he doesn't nap, but he does need to learn to rest in the cot without your presense for an hour' - like what Katie suggested - give a cut off. I think going in there and continually repeating/telling him to go to sleep will get you more stressed and him more wound up. How about if you put on a lullaby CD (I still use one for my DD to fall asleep) and put it on for an hour or so and if he's on his own listening to the music he might relax into sleep - clearly he's tired. Also totally agree with PP about us being the ones who have to be in charge and we can't always keep them happy, but of course we do our best. My clinic nurse (who I trust so so much as she is amazing and has about 30 years experience, plus has read and loves BW) told me that by locking the door (which is what we had to do to keep DD in her room) took away the emotion and actually made it easier on the child. So in my situation, me standing outside the door continually repeating, 'go to sleep' didn't have the same effect as, 'I love you, it's time for sleep, if you don't sleep then you must rest in your bed and I will get you up in an hour, when the music CD stops', then I walked away and it made her job of falling asleep so much easier. I certainly don't think I let my DD CIO, I just made it very clear that if she wasn't going to rest/sleep, then I was... I have a very good friend who's DD is far more spirited that mine and she did the same thing every day, put her girl in the cot for 2 hours and although she didn't sleep, she played, after about 2 weeks her daughter went back to taking a 2 hour nap. Even if he doesn't sleep, but learns to relax in his own company and be happy and secure in his cot (which is really important) you will get a rest and a break. He may be picking up on the fact that you are losing a bit of confidence with the sleep thing as kids are pretty perceptive so as much as he's not trying to manipulate you, by being confident with him/looking him in the eye etc when you explain what is going to happen, he will feel really secure in what you are doing... Another thing is, what's his environment in the room like? Is it pitch black? Maybe if there was more light in the room, it might be more relaxing for him. I found that my DD didn't need the room to be pitch black for naps as she got older, in fact she napped better with a lighter room. Another thing that another friend uses for her DD is an audio storybook for nap time. It plays for awhile and she swears by it, because she says when her DD is protesting her nap she just tells her she has to lye in her cot and rest and listen to the story - her daughter ends up falling asleep to it - takes her mind off the protest. It is not unusual to change the environment for sleep as they get older. My DD used to have white noise when she was little then as she got older we went back to the Music CD, then she just told me herself, 'I don't want the music, I like it quiet' and that's how she wanted it, so that's how it became... Might be worth changing something?
Once again, big big hugs. It's incredibly hard when they don't sleep and you worry that you won't get out of this, but tomorrow is another day. Try and get some rest if you can...