If he is refusing a 2nd nap, could you just push until 12:30 when you can actually get him down and then do a short A to bed? I agree with Liz that with such a long A to bed, it can really mess up the night. My friend is in a similar situation with school drop off/ pick up and since her LO refuses a 2nd nap, she just goes with the afternoon nap and the shorter afternoon A. Although, sometimes her LO falls asleep for 10/15 minutes in the car in the morning and then still goes down for the 2nd nap fine. So the car ride actually AP's her LO into a morning nap. Could that work for you?