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The trick is not to get sucked into buying a game just because it looks cool. All the games "look cool" on some level. Research an upcoming game that looks good to you, in a genre you like, and when it comes out play it. Play it until you're finished with it (either completed or just done with it and won't go back to it). Then and ONLY THEN, do you go out an purchase another one. If you play games in any sort of regular manner, then this system should work fine for you. And NO GAME will ever reach the "vintage expensive" state before you get to play it. If a game gets that old before you get to play it, then it wasn't one you really cared that much about in the first place, and will most likely be one that you start and get bored with.

On occasion, their will be more than a few "must have games" out around the same time. In this case, pick your most favorite of the bunch, buy it, play it, and then save the purchase for the other game(s) until you are ready to play it. Then it will either be cheaper for you to buy (yeah!) or you won't care about it anymore, and no money or time is wasted.