Speedy inflation

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You can blame Rolex. As the 'hot' refs have become out of reach for collectors, many are migrating to Omega.
 
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I don't know if that chart is accurate, but I do know that there are people on the forum who have tracked forum, eBay, and auction sales of vintage Speedmasters comprehensively. There is a thread somewhere that used to be updated periodically with a record of sales over the past month, or quarter, but I can't find it easily. Also, William's pricing chart on his website has been updated monthly for a long time.
 
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I’ve always believed that prices have increased largely due to expanded scholarship for some of these references.

You could argue social media is driving this from a demand side, but I think resources like OF, Fratello, and Moon Watch Only have largely gotten rid of any information asymmetry for these references. People are more comfortable paying $10k, $20k, $100k for a watch when they know the watch can be verified to be what it is (serial#, dial, case, pushers, etc).