I'm not anti boarding prep school at all (I work in one) but, in this case, I would be concerned to be honest.
It's not necessarily your child that would concern me, it's the school.
I am particularly worried about the following:
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Your son phoned you sobbing uncontrollably. That in itself is not unusual. As we all know children get disproportionately upset over small things and both crumble and cheer up incredibly quickly. It's the fact that you don't know what happened next that worries me. Where I work there are no phones so far from adult ears that we wouldn't hear distressed crying. We never interrupt a child's phone call but we do scoop them up when they come off the phone, calm them down, go as far as we can to sort out the problem in that moment and then, most importantly, call the parents back to reassure them that the situation has been/will be dealt with and their child has gone to sleep calm/happy and not cried themselves to sleep.
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The 'curt' housemaster. That's no good at all. Even if he was stressed and busy at the time. Full boarders and their parents need the utmost care and sensitive communication. Anything else is unacceptable.
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The lack of response to your email. Our policy is that general parental emails must be responded to within 24 hours, even if it's just with a 'thank you for your email. I will look into this and get back to you with a full response as soon as I can.' But emails from parents of boarders must be responded to within 4 hours, no longer. It just isn't okay to keep a worried parent who can't get to their child, waiting.
If you genuinely feel that UK boarding is right for your son and your family, I would take him out of this school and back to New York for the rest of this academic year and sign him up to start at a new school in September at the start of Year 5.
Starting a new boarding school for the Summer term or even earlier will make it much harder for him to settle. The other children will be in established routines and not struggling with the things he will find hard when adjusting. Year 5 is a common and well established starting point in prep schools and there will be other new children for him to get to things with.
On a slightly different note, I'm surprised to see such low figures for young boarders that include flexis. In fact they're almost unbelievable:
Last available figures are for 2014 - page 29. (boarder defined as having boarded at some stage in the autumn term) Across the UK: 87 - 7 year old boy boarders. 377 - 8 year old boy boarders. This is not something that UK families do any more unless there are very special circumstances at home
We currently only have 1 full 7 year old boy boarder. Which seems to fit the statistics. But we have 3 7 year old girls and 1 7 year old boy who do three nights a week and 2 girls and 4 boys that do 1 night a week. Looking at the register there are a further 12 7 year olds who did one or two occasional 'babysitter' type nights last term. Do they count in the figures? because, if so, that's a total of 23 7 year olds out of a year group of 35 who 'boarded at some point in the Autumn Term'.
That's around an 8th of the total of the whole country (assuming similar stats for girls) - from one small rural prep school. That seems ... unlikely in the extreme!