Castlevania Timeline of course

Physically acquiring a brand new, sealed copy of Dawn of Sorrow was damn near impossible in AU, for non-extortionate pricing through a retailer - that’s one win. (This was due to Atari distribution ordering too few copies and botching Konami’s au supply at the time.)
In-game achievements would namely be completing POR(regular & sisters mode) & OOE on level 1 max cap hard mode, as well as getting to Dracula with Richter/ Maria & Albus, respectively, in the same mode. (EDIT: Getting some of the boss medals, in particular rebooting the save file and then being rewarded with the Dracula medal felt pretty bada$$).
Beating CV Chronicles for PSX and especially killing that damn werewolf(stuck on the most difficult A.I. on the PlayStation version) with the triple-cross was also a huge monkey off my back.
Lastly, back in the day before speedrunning was a thing, blitzing LoD and finding all the lost children in Henry’s mode was satisfying.
EDIT^2: I was going to create a separate post for this but cbb: Dreaming about OOE approximately 5 years prior to it’s release. Call it a vision, prophecy, or whatever.(… Eerie, I know)