I haven't thought all that much about Simon's sleeping habits, or the time around when he sleeps, in the recent past. I think that might be good. It is worth noting that we've made some changes lately.
First off, bed time is getting a little bit better. He's at least willing to brush his teeth about half of the time. We've even seen a few occasions where he knows he's tired, and voluntarily climbed into bed in the afternoon or evening. I think a lot of the problems around sleep is that he just doesn't want to miss anything, but he's starting to understand the value and comfort of good rest. That's certainly a relief for us.
We're also limiting and reducing naps. After our week in Seattle, with the time changes and all, Diana is generally keeping him up on school days, Tuesdays and Thursdays, though making room for exceptions when he obviously needs a little rest. He doesn't get home until 2:30 at best, and his late naps were clearly affecting his overnight sleep. When he does nap, we're not letting him go two or more hours. The length is still fluid, but 90 minutes seems like a sweet spot.
He's going to bed by 8:30 most nights, though later is OK when we're traveling or we go to Cedar Point in the evening. He seems to be rolling pretty well with that. He's getting up in the morning a little later, but I haven't been paying enough attention to see how much later. All I know is that I've sleepily noticed Diana still in bed with me a lot of mornings when my alarm goes off just before 8. That sure beats 6!
Simon is really growing up fast, and seeing him start to transition to a kid who understands what bed time is about is one of the things I won't mind. One sad point, however, is that he no longer wants to sit on my lap to read books before bed, as he prefers to sit in his own chair. On the bright side, he does seem to like to cuddle more when watching Sesame Street.