Interesting topic - and who hasn't tried to figure this out?!
I have had great luck just before Christmas on eBay, and at local card shows. In fact, the closer to Christmas, the better. Got some great deals on set breaks on eBay for my '69 and '72 sets. After New Year's, not so much. In short, I think holidays are a great time to pick up bargains. (But not while you're drunk - stay away from eBay when you're drinking!!)
It's funny how weird little things will spike prices. When the National offered those Diamond Stars of Ruth, Gehrig, etc. it seemed like every dealer raised his prices on the originals by 50%. Seems like it's finally tapering off a bit now.
Sunday nights on eBay are tough. Mondays seem to be much better.
Personally, I haven't noticed a difference for in-season prices for vintage, unless a particular player is in the news - like when Bobby Cox made the hall of fame.
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