Jason, I think your post touches on something important. I think it all depends on what you collect.
There are collectors on this board who purportedly have been searching for specific cards for decades. When a copy turns up, no matter how badly conditioned, I'm sure they'd be happy to own it.
There are just some sets out there that finding specific players is extremely difficult so condition becomes significantly less of an issue.
On the other hand, it also depends on the number of people actively pursuing the set. Your own example of T206 illustrates that. Whether gem mint or roached, there will be a buyer for any individual T206 card. A wide range of price results however.
The more available a certain issue is, the more scrutiny they undergo, as another example is right around the corner.
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