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no, this is not possible now. I would discourage you from attempting to send an email to all of the email addresses a lead lists. this will certainly annoy them.
I am not quite understanding the question. If the student uses their current college email, then why would it cause a dupe?
if they use more than one address, then yes, a new record is created. You'd have to use DemandTools or RingLead to merge those automatically. You can retain the old email if you create secondary email fields. But you won't be able to email to that secondary email address.