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[TheScarfedOne]

For sending the bulk messages to parents - I would suggest looking at dedicated products such as Groupcall, ParentMail, Teachers2Parents etc (search the forums for these - there are plenty of discussions on the merits of all). These systems will all maintain a record of contact, use the details maintained in your MIS, as well as reduce the admin overhead of actually doing the message/grouping parents to send to.

[InterwebsGuy]

Wouldn't you email parents using BCC anyway? If I understand (and remember) correctly that then counts as sending only one email?