Mike, there are two entirely separate issues here. One, on the surface, is prefectly legitimate. The chip on the left here is a classic. It has everything going for it, great condition, attractive inlay, small key, inserts, history. It's a gorgeous chip. Our good friend Dean Clark has a "scarce" one on eBay right now, he'll be doung well to get $5 for it. Because, for all it has going for it, it AIN'T scarce!
The chip on the right strikes me as a rather dowdy hot stamp, a bit on the used side, and you'd do well to find one for $100 if you find one for sale at all. Rarity is definitely a valid driver of price.
The biggest problem with your slabbed coin is that the "rarity" is artificial, created and supported by the slabbing process. I prize better quality chips over worn chips, and will generally not balk at paying a reasonable premium for quality. But true rarity is not one coin with fewer bag marks than its millions of sibblings.
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