About the taxes. When you win a prize over $600, you receive a 1099 that will state the value of the prize you've won. Sometimes you can run the numbers yourself and find the prize is actually cheaper than what is on the 1099. Then you ask the issuer of the 1099 to adjust the amount on the 1099 after you provide them the documentation of the prize actually being valued less. Whatever is on your final corrected 1099 is what you will pay taxes for. In reality, I think you should expect your prize to cost about $2,000 in taxes, just as a previous poster stated. Still less than you would actually pay for a family trip to WDW.
Also, I was reading a few days back that few sweepstakes winners realize that you can decline portions of the prizes. I am
not saying that is the case for sure in this Disney sweepstakes but it may be. That way one could elect to keep the portions of the prize that they desire (for me, the hotel and park tickets, and maybe airfare if I went to DL) and decline others (I might decline the $500 if it could not be applied to food because I don't want a spa treatment, tour or a lot of "stuff". I might prefer to drive myself and the girls to WDW even though it's more than 250 miles because the cost for me to drive is still probably less than the taxes would be on the flights etc.
Again, I don't know if you could decline portions of this particular sweepstakes but if you can, it could keep the tax bill down a bit if there are parts you don't really want.
If I won, I would figure it would cost me in taxes the cost of one of my usual bargain trips if I got nicer accomodations and less than my bargain trips if I received value accomodations.
Some sweepstakes/contests include a cash gift to help offset the cost of the taxes. That is a great bonus.
