Your error is in assuming that Woody is rare because few Woody dolls were made. Not the case: Many Woody dolls were made- and because of their popularity they were sold and played-with until they were wrecked and - this being the 50s - thrown out. That plastic Woody you’ve got there will outlast most civilizations: but our Woody? With his cloth body and its aging 1950s fabric? By the 80s most of those would be a wreck: cloth-body stuffed toys have a very short shelf-life once they’re out in the world. Store a Woody in the attic for ten years and the mice get him, or the mold, or the simple weight of time loosens the bindings and makes his limbs unravel. And the voice box? With an in-tact, still functional draw strings? Do oyou know how often those things jam?
Woody is unique because he seems to have belonged to a family that takes unusually good care of their toys, going so far as to fix them. Toy from the 50s are not in any way shape or form equivalent to modern full-plastic toys or even BEanie Babies, which were sold primarily with a view to the long-term collectors market. There is absolutely nothing weird or strange in a Woody doll surviving in such good quality to 1999 being notable: his popularity and high production rate has zero impact on the toy’s long-term survivability. (Indeed, that high production rate could have even introduced a lot more manufacturing defects into shipped Woody dolls, creating an overall decline in quality.)
Just because it saturated the market is no indication of longevity. Yes, Al sure has a lot of Woody stuff - and most of that is very rare. For a good comparison point hop over to ebay and start looking for vintage, no-package Howdy Doody dolls from the 1950s - not the 70s re-releases with 70s materials but the 50s ones. Start judging the quality: the faded fabrics, the dirt, the smudges, the dinginess, and you’ll begin to see why Al freaked out so much: he didn’t just just find a Woody with a hat, he found a Woody who was clean - with no chipping on the hand-painted face, whose hand-stitched hat hadn’t lost its stitching, whose arm break could be repaired by a master who knew what they were doing. A hundred thousand Woodys might have been made in the 50s - but the number that survived to the present day, out-of-box, out of the hands of collectors, in good enough shape to be polished-up into museum-quality condition?I
Al found the treasure of a lifetime.