@foxrye: Any advice regarding whether or not you should transfer depends upon your specific reasons for wanting to transfer.
I have read several of your past posts.
Without knowing more about your concerns at this time, if you have multiple leadership positions you should probably remain at Loomis Chaffee as this indicates acceptance and involvement as well as a committment to others. But, as I noted above, it depends upon your specific concerns and why you think that Peddie or Hotchkiss or any other school would be a better fit for you.