I would speak to his carers for sure- they would be in a position to give you some good advice about his skills in that environment.
You know your son best so I can't answer really based on him as I don't know him, but I would err on the side of keeping him back a year. I think school readiness is more about ability to cope in social situations and emotional skills plus self-help skills such as dressing, rather than leadership (which as you said is personality based) and academics. I'd also be taking what the principal of the school said as important too- perhaps you can find out if his advice is what most other parents are doing? Then you'll know if your son is actually going to be the oldest or if other children his age will be held back too.
My son's birthday is in March and children born Jan to April here can either go to school younger or older. We will be keeping him back so he is older and this is also what the majority of families in our area do so he wont be the "older one" iykwim. I also don't see the point in rushing to start school- some cultures don't start formal education till 8. Why start at 4?





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