T.S.
Re your response to Margie G and "other comforts" the fact is (or was, at least for me) that there are no other comforts that satisfy like the boob. Of course there is discomfort when that is stopped. But that's just a normal part of parenting isn't it? I was also a long time, on demand nursing mom, but I wasn't interested in nursing them into kindergarten, so of course there were some tears as we adjusted from boob to story time. And I really didn't stress about food, because even when it felt like they were barely eating they were still thriving and growing. I also LET my kids nap in the car. We were a family on the go! There was no way I would wake a napping child. If we got home after five minutes of sleep the kid stayed in the car, windows down and in the shade or garage of course. I think you just need to relax about the food stuff, stop trying to make naptime a perfect routine and possibly start weaning. He is miserable because you a trying to make him adherent to your predetermined schedule and expectations. Just love him, feed him (as much or as little as he wants) and LET HIM SLEEP. The whole family will be happier for it.