No issue with your hypothetical OP, - would probably prefer an older sibling to go with him but that's just me - safety in numbers.
But, and I have never understood this, why do schools want books picked up prior to school going back?
It makes no sense. Where is the efficiency gain here?
DS's school issue all the books in the first week back. He will, in the first week, come home with a clutch of books that need to be covered (covers provided together with name labels) and we are expected to cover them and send him back with them over the following week.
I don't get it. Maybe I'm missing something.
Children arrive first week back, school issues books. That's the way it was when I was going through primary - NZ admittedly but that shouldn't matter.
Disclaimer: I am not talking about High School and electives. Different ball-game. The OP's son being 10 1/2 means he is still in primary.