Jbald, I guess the answer to your question is- sometimes. There are caring Rabbayim out there who will stay in contact. My favorite story was of a 9th grade Rebbi who had a student who was asked not to return for 10th. (And yes, the hanhala was involved in finding him a more suitable place.) The Rebbi gave his student his whole collection of old hard cover Hardy Boy books that he had from when he was young as a parting gift and to maintain a friendship.
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