Originally Posted by RawAlex

If you want to one up it, give away what hasn't been given away before...

Vacation home in Thailand or Cabo or something... maybe "vacation for life" share of a timeshare condo somewhere decent...

You could do trip around the world, charter a private jet for the winner and X of his or her friends to go anywhere for X number of days, example.

Webmaster shows on us: Passes, travel, and hotel for all the top webmaster events for a year.

"U-haul trailer full of cash"...

Reverse hookers: Send over a series of hookers that pay the winner to have sex with them.

There are so many interesting options.