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When we were pregnant with Bella, Will entered giveaways constantly. He set aside about 4 hours a day to just sit and enter giveaways online. We won SO MUCH STUFF... Like, 3 designer crib sets, a $600 rug from Shaw Rugs (which we traded to my mom's sister-wife for an XBox 360), a Soda Stream, tons of outfits and baby clothes, a croquet set, $1000 from a publishing company, etc. The UPS man was stopping at our place at least twice a week. We sat down and added it up when he decided to stop entering and we'd won something like $6000 worth of stuff in a little over a year.
Moral of the story? You can't win if you don't enter.
I won $1000 from a radio station once...when I went to their bank to cash the check, there was some problem with their account (overdrawn...hahahaha) and the manager had to come and approve the transaction.