S.F.
You mentioned 8:00 bedtime. Is that the time you start the routine or that he's actually in bed ready to fall asleep? I have a 3 year old daughter, and I've been finding that I need to get her to bed earlier than we have been, which is about 8-8:15 of actually falling asleep. We start it around 7:30-7:45 most nights. There was just a huge article in the St. Paul paper about kids not getting nearly enough sleep these days. Maybe he needs to be in bed earlier? I'm a firm believer in each child having a sleep window and if we as parents miss it, we are going to pay for it! Maybe a little earlier will help hit him when he's actually tired and ready to fall asleep. Good luck!