Happens all the time. Go for it bro. I'm assuming you are adding these users to your mailing list? Just make sure your newsletter emails contain proper unsubscribe info.
To cover your tracks just get one of your friends to submit their email addresses. You can say they were the winner of the iPad. If FTC comes knocking just get them to play along.
Or just give someone an actual iPad and send it return receipt requested. Also ask them for a picture with it and few sentences saying how great you are.
What if you don't have $499?
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