I thought the w house system was comforting if you hadn't boarded before or you came from a small prep school. Also , the slight scruffiness and the hm's dog made it feel very homely. Ds liked the idea of his toy.
Ds took a scunner to the matron and the twyford crew, alas. I know he would have been happy and thrived now, though he woukd have had a tough 2 initial years, and I still feel that issue about maths for the moderate, and have just said to DH I still regret him not going there. DH, a wickhamist, disagrees and thinks that the initial misery would not have been worth it and that Ds dis not want to board was important.
Again, it is about the right school for the child, as hg knows so well, and I would suggest you take your Dss ' views seriously. It will be their lives and I think the days of I went there so you must should really be over. Their instinct, even if badly expressed , is useful.
We came down to two schools with Ds, one boarding, wc, one day. Both had the features and characteristics we were looking for in principle and excelled in slightly different things. We then discussed with Ds over a period.
What is right and how to approach it will vary from.family to family and child to child.