Sorry, cc = controlled crying. So it's fine to leave him to self settle, but if he cries an "I need you cry", go straight in to him and shh/pat rather than leaving him for a set number of minutes. I think it sounds like that's what you're doing
What time are you back from that afternoon school run? If you can push out the morning A time and get a good morning nap, you could probably do a short nap after the school run, so something like this:
WU: 6/6.30
nap: 9.30 - 11
nap: 3 - 3.45/4
bed: 7
Or if that won't work, you could go for a capped am nap and try to get a long pm nap in before the school run, then slightly earlier bedtime if need be:
WU: 6/6.30
nap: 9.30 - 10.15
nap: 1.15 - 2.45
bed: 6.45
That would work better with the 11am run too. What do you think?