Popup triggered on product tag, and e-mail notificaiton by Evan McCarthy

Hello, I am looking for simple functionality that will do the following:

1) When a customer starts to check out with a product that has a specific product tag (string), a popup window with a message is triggered.  (the user just closes it after reading)

2) In the order confirmation e-mail, if a product has this specific product tag, then a customized e-mail is sent.

What is the best way to do this ?

Thanks

Evan