I'll stick with this gen, though I'm a more prudent videogame buyer these days (internets is good for something) ....
As of now, I'd say I regret buying The World Ends With You (sorry to fans of the game, I just cannot get into it).
I regret paying FULL RETAIL VALUE (50 + USD) for House of the Dead: Overkill, MadWorld, New Super Mario Bros. Wii.
Not that I didn't enjoy these games, but they don't have much replay value and are collecting dust.
GETTIN' CHRONOCRUNK