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I'm not a teacher, in fact, I'm a recently graduated high school student, but I DO have 6+ years of experience in theatre, most often with Shakespeare's plays. I think that the easiest of Shakespeare's plays to introduce students to first is Romeo and Juliet, mostly because that is the most popular one, and there's a good chance that they may have seen Baz Lurrman's Romeo + Juliet, which will act as a kind of bridge for them to cross to better understand Shakespeare from the begining. Consequently, the hardest one to use as their first taste of Shakespeare would be A Midsummer Night's Dream, and the main reason for that is that there is so much mistaken identity and "drama" between The Lovers that it's difficult for them to keep track and try to learn more about Shakespeare and his plays in general.