Hi there, I'm sorry you haven't had any replies yet.
It looks like you're well into the 2-1 transition, but on that current routine he's probably getting rather OT. Generally you don't want the day to be any longer than 13h, which would mean in bed asleep by 6.30pm if he is waking at 5.30am. The rolling around at BT could well be that he has got a second wind and can't settle. Have you ever tried putting him down that early? He may still wake at 5.30am but that would be a solid 11h night which would put you in a better position to try to push your day later as he will be more rested. What do you think? If you give it a go for a few days and you are still getting BT resistance, you could try cutting the pm nap to 20 mins and again aiming for 6.30pm BT.