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Johh H.I'm a collector of sports board games so the steals that jump to my mind are mostly in that area.
Back in 2000 I bought a mint 1962 edition (1961 season) APBA Baseball game from an obscure auction site for $45. It had been on there for months but I was hesitant because the description wasn't very detailed. I pulled the trigger when the seller offered me a money back guarantee. A couple of years later I won a mint 1961 edition for $82 on ebay. Both games were in absolutely perfect condition. What a thrill to handle those virginal pure white 40+ year old cards.
About 18 months ago I saw a 1964 Challenge The Yankees game on ebay with a Buy It Now price of $135 on it. CTY usually sells for $500-$700 in decent condition. The scans looked like it was in nice shape but the description made it sound like a well used copy...almost a beater. I figured that, seeing as it was complete, it's still a great price for the most in-demand baseball game of the past 50 years so I bought it. I emailed the seller for more details and he still said it wasn't a game for anyone fixated on condition. Well, when it showed up a short time later I was in absolute shock. It's probably one of the two or three best condition CTY games to show up at auction in the last 10 years. Even the box with the gorgeous painting of old Yankee Stadium is in superb shape. An unbelievable steal for $135.
One more baseball game story. Just over a year ago there was a 1966 season American League version of Bamco's Hank Bauer Be A Manager game listed on ebay. I only found out about it because the guys on the Yahoo Baseballgames group were chatting about it. This is a rare game that usually goes for anywhere from $300-$700. I put it on my Watch list and waited to see what would happen, not expecting it to remain in my price range for very long. Minutes before closing, I was shocked to see it was sitting at only about $130. I figured that the snipers would start inflating that at any moment but it never happened. Finally, I threw in a bid of something like $150 or $175. I won it for $135! I think the next one listed sold for $660.