One of the very few things I dislike about playing games on modded consoles / emulators or pirating games is that it's a lot harder to go back and tell when I started & finished a game.

Tracking when I start and finish games is surprisingly important to me, so it's a huge deal when I can just pull open my Sony account and see trophy timestamps from 8 years ago.

I was able to track approximately when I first played pirated Skyrim and FONV from nexus mods download history, give or take a couple months but, for all those others I played stock, there's no telling. Unless I kept the game files, there's not even a record that I played it at all.
For some reason, it's a lot easier to remember my childhood if I think about it in the context of what game I was playing at the time.
(that said, I'm still desperately trying to recover my old live email to access my xbox360-era xbox live account and I may or may not be able to)
That puts the furthest back actual achievement data I can get my hands on at Dec 25th 2007. Frankly I can't remember too much about the games I played before then aside from some heavy hitters​​
@dfxluna Welllllll....
https://retroachievements.org/ :3

The only sad thing is that the list of supported emulators is a bit limited.
RetroAchievements

Adding achievements to your favourite retro games since 2012