Man, where do I start? Passed Street Fighter Alpha 3 for Star Wars Episode I Racer, both for the Dreamcast. My logic? Well, this was a clearence of brand new Dreamcast games, two for less than 14 dollars. So I wanted to get 4 (I choosed SF3 Double Impact and Jojo). And I tought, why should I get Street Fighter 3? I already have it as a japanese bootleg cd-r for the PSOne, and I wanted something new that I have not played yet. And I already had two fighting games. So I went with Star Wars. Probably played the first two or three circuits. Didn't like it. And today, in this country, you are lucky if you can find a used SFA3 for 40 dollars. Damnit. Also, saw a ton of Virtual Boys brand new on some Toys R Us in Texas for about 14 dollars each back in 97. I already spent that amount that day in some Calvin and Hobbes trades, so I decided to get the Virtual Boy the next time I would visit the US. At that point I was used to visit the US at the very least two times a year, sometimes three. It would take me 4 years to return to the US. And before that, every time some friend or familiy member would go, I would ask them to check if they still had it, new or used, I didn't care. No one came trough. And yes, the cheapest Virtual Boy in used condition I have found here is about 80 bucks. Grrr! Sold my entire collection of GB games back in the day to get money for a comic convention. I still have the comics and I did have fun there, but God, that was probably one of the dumbest decisions I have ever done. I had many games in boxes,complete and sold them to a reseller for very little. I only have two from those days, complete: Tetris and Raging Fighter. And for some reason the box and manuals from Taitos Adventures of Star Saver. Found a lot of used and new copies of Rayman 2 for the Dreamcast, quite cheap. Passed. Haven't found it again here. Also passed on a 12 dollars used copy of Beyond Good and Evil for the Gamecube. Later played it on PS2 at a friend's. Such an awesome game. I remember not getting it because.."it didn't come in the box" Traded a NES game, California Games, and cash for a bootleg Street Fighter 2 for the NES. California Games was fun and that game belonged to my older brother, and I still took it without his permission. That crappy Street Fighter game was the punishment I deserved.
Yeah I know and it was well reported so when it got released, which was hy I bought it. It's not that hard to find second hand, surprisingly. In fact, up until very recently the local Gamestation store in my home town back in the UK had a copy for sale for about 15 GBP (no point converting to $ because it doesn't work that way back there). The main reason I waited on PDS was that Sega Saturn Magazine gave away the complete first disc "free" on the cover in place of the usual demo disc. I still have that somewhere.
Man, i got owned way too many times to pick a worst one. but probably most reciently was paying $60 for Taiko Drum Master, and seeing it about a month later for $9.99.
My favorite: When I was younger, I read a magazine that mentioned Sonic 2 was about to be released in July(can't remember the year exactly). A friend of my father was going to Paraguay(at that time, it was "THE" place to get new games). Well, he came back and luckly, he bought one to me. After my dad brought back those games home, I couldn't wait and inserted my brand new Sonic 2. Strangely enough, it didn't last more than 5 minutes and at that time, I thought it was resetting my mega drive. I could even play with Tails with a second controller. But most important, it seemed like it wasn't finished(*). After three months without any reason, it crashed and I used it as keychain for a long time before I lost it for good. (*) = Several years later, I saw an ebay link with a huge RARE*Prototype Sonic 2 Beta Cart* reaching way above U$1k and got me thinking, how stupid I was.