OK, from the advise you've given, here is my plan for next week. Tell me what you think.
1. When he wakes up at 5am, I will leave him until he starts to fuss. When he does, I will feed him, change him, and just have a quiet time until he seems tired again. I will try and keep this first interval of awake time brief.
2. During naps, I will attemt wake-to-sleep again. I've tried it for every nap for 2 weeks each time I've done it, but It's been over a month since I attempted it. Perhaps he is older now and it will work. In the past, I've tried both waiting until he stirs and going in before he stirs. Neither worked, but I think this time I will attempt going in before he stirs. I just don't see waiting until he stirs working because he is too aware that I am in the room at this point.
3. If he wake from a nap early and is content, I will leave him by himself for quiet time-- What should I do when he starts to fuss?
4. I will try and extend his awake times, other than the first interval, so that he is only taking 2 or at most 3 naps a day.
What do you think of this plan?