My biggest regrets on buying all involve around pricing. There are a bunch of times that I negotiated myself out of a rare card because I was a cheapskate. I would push the seller down and down again to try to get the best price, and in the end, he decided to sell it to someone else, and I realized that I should've just taken his offer. Similar things with setting snipes on ebay. Sometimes, I figure this card will go for a really high price, and I can't really afford it, but I'll just put this lowball snipe out there just for the heck of it. In the end, the winning bid is just one increment higher than my snipe, and I'm in shock. I would probably still have lost, but sometimes, it's hard to get over the thinking that if you had just bid a little more, you might have won the card, and it might not have been a total steal, but it still would have been an extremely good deal.
There's also the flip side of course, where I don't know what I am thinking, and I overbid for a card, especially those that aren't even rare. I've done this so many times that I kick myself and promise that I'll be tougher w/ my buying in the future. That of course, leads to what happens in the previous paragraph.
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