As for the iPod problem, they have an interesting solution here in the ‘burbs. The teacher will read off the contents from the iPod the first time, the second time, he synchs it to his play list. Being that he’s an absolute fan of the worst jazz music ever created (I don’t even know how they get away calling that ‘jazz’) it is a fate worse than death.
Mess up the play list! Erase it, even--
Good solution, but there’s an ACLU type waiting to sue you for infringing on the student’s right to listen to anything they want whenever they want.