mom2rtk said:I don't win. But then I don't play.
OP, I've seen a number of posts from people who won trips or special experiences post on the DIS. That said, the odds are astronomical against you winning, so you need to let your son know it's not likely.
I have this really funny tendency to win 7th or 8th prize when I really want the grand prize. Observe:
I entered to win a trip to the Walt Disney World marathon and won a pair of shoes.
I entered to win a trip to Disneyland and won a Cars coloring book.
I entered to win a Disney Cruise and won the soundtrack to Tangled.
And my absolute favorite:
I entered to win a trip to Aulani and won a hulu dancing Olaf figurine.
My husband and I won the Family Time Resolution sweepstakes last year. It was a trip for 4 people for 5 days/4 nights and it covered airfare, hotel, park tickets (with park hopper), and a $500 Disney gift card. We got to pick any resort on Disney property to stay at, so of course we chose the GF! Since it was just the 2 of us, we were allowed to make our trip for 8 nights instead of 4! Disney was wonderful to deal with! Now I enter a ton of contest since I know it's possible to win!!
about.com has a sweepstake page and I also like sweepstakestoday.com, they have lots of sweeps listedWhere do you find these contests to enter? The only one I've seen turned out to be the GoldRush Getaways scam.