Molly-
I won't presume to help you fix all everything in this message, but here are a few things. If he is a young baritone, (under 25!) be patient getting the top range. the male voice "mutation" is VERY different from the female, and it is not uncommon for it to take many years before the whole range is there.
Make sure that at least some of the repertoire is masculine and robust. This will make him feel better about singing, and will help get the right sound. The "First Book" series has many such pieces.
As for piano, PRACTICE (of course) and try to assign pieces you can play. Many books now come with accompaniment CDs as well, which might help as you get closer to performance time.
Good luck in the wonderful world of teaching!
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