>>108447721In the second movie, Al and the Japanese guy talk on phone, and Al asks "imagine we added another zero to the price, huh?". The guy on the phone is heard replying "I'll pay anything you want". So I've assumed that Woody's value is something insane; on a similar tier as those Nintendo World Championship Gold cartridges, or maybe even Action Comics #1.
However, Woody was a used toy who had suffered some damage (the burn mark on forehead, writing on his boot, arm ripped off), but he also got restored during the second movie. Both the damage and the restoration work mean that he wasn't in mint condition. He wasn't inside a package either (assuming he used to have one). So if there were a Woody toy who had never been played with, he'd be even more valuable.
>>108452174The guy who was selling him didn't know about the toy's history. He sold Woody with the vague title "Cowboy Doll", and he was surprised to find out that someone was willing to pay $2000 for him. Maybe not too many people saw the auction, and those who did lacked enough funds for their bidding war. The results would've probably been different if the title for the auction had been something like "Rare Vintage Woody The Cowboy Doll From Woody's Roundup 1950s Great Condition".