Probably the original Sonic games on the old Megadrive/Genesis, bought them back in the 90s, then bought compilations with them included a bunch of times on various consoles afterwards..
Also the Sonic Adventure games, bought the first Adventure title on Dreamcast, bought the remastered DX version & Adventure 2: Battle on Gamecube, then the ports for the Xbox 360 several years ago..
Then there's Payday 2 on the Xbox 360 & i sunk ALOT of time on that game only to realise us console players got royally screwed because we had missing content & wasn't up to our PC brothers & sisters version, bought it for Xbox One years later as we were promised a more up to date version of the game where it was finally up to PC standards with all the content that was never ported to the 360/PS3 only to realise later that we got screwed yet again.. If they ever release a new new "ultimate" version on next gen promising us the world, you bet your sorry sweet ass i'm gonna buy that piece of sh3t again, am i crazy for buying it two seperate times & not learning a lesson?.. crazy enough to be screwed by the developers for a third time, aww yeah. <;}