What if there really was a Woody's Roundup show?
Then a well-worn Woody with a repaired arm would not be worth much. Even one in excellent to mint condition should not be too hard to find, compared to the Horse or an unopened Stinky Pete. That would be the real jewel of the collection.
Being the star of the show, there should have been tons of Woody's sold, like all of the Buzz Lightyears in the Toy Barn, so the large supply should keep the price down. The only thing that could have driven up the price of Woody would be if he was part of a series that was discontinued. For example:
His spurs could have been made of metal and could have sparked like Rollerblade Barbie.
He could have said something politically incorrect when you pulled his string, like talking Barbie ("Math is hard") or the swearing Furbie.
As shown in The 40 year old virgin, it was not the Six Million Dollar Man (Steve Austin) figure that is the most valuable, but the Oscar Goldman.
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A dope trailer is no place for a kitty.