((hugs))... school runs can be such a pain, especially during transitions!
Our school runs are 8.30-9am and 3-3.30pm. With us, dd3 needed to transition to 2 naps around 5 months and she used to almost always fall asleep just as we were back home from the morning school run. I used to take lots of toys with me and sing songs/distract her on the way home (just a 10min ride but enough to make her dose off
) and that worked really well. Some days she would get really close to falling asleep but she was pretty good at continuing her sleep in the cot, as long as she wasn't in "deep sleep"... only if she was in the early stages/drowsy state I was able to transfer her. Could you try and distract him? With us, school starts at 8:45 but from 8.30am children can be in the playground and under the supervision of teachers and I do remember dropping the girls off earlier for a few weeks as she was getting used to more A time... would that be an option for you?