I enter sweepstakes all of the time. I used to enter exclusively by postal mail but that got way too expensive. Now I enter on-line. It's faster and you can find great prizes. Today I found one where you can Get a Free iPod from iPodSweepstakes.com Now!.
They give away one ipod every day. How does this work? You get one entry just for your initial sign-up. If you don't win the daily sweepstakes, you can earn one. You get points for completing advertisers' offer on the site, by clicking on emails that they send you or by referring a friend to the site.
I'm signing up for this. If I don't win the daily prize, I can always accumulate enough points to earn one.
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