I think for me it’s Harvest Moon Friends of Mineral Town. Even though the triggers can be a bit bugged at times the achievements act as a great way to track progress like character events and your relationship level with people of the town. It’s not super hard to check when dealing with the bachelorettes because their heart level is shown but seeing exact percentages is nice.
They have also incentivised me to play a lot NES games I may not have normally played like Abadox.
I was a big fan of the meme sets for the Mario’s Early Years games and rushing to get into the top 10 before my friends when they dropped. We did it live on our channels and had a voice chat going on. Good times!