Yeah... I'll say it:
Pokemon.
I know Gen Wunner's is a thing, but it's gotta be a stereotype for a reason.
Gen 1 for Pokemon had a ton of problems. Type Balance, Type Combos, Pokemon Diversity, just straight up bugs in the code that broke the game.
And yet, something about that game really feels like the easiest to go back and play multiple times.
I try to replay Gen 2, but the XP grind is such a pain, and the Dark type is scarce AF.
I try to replay Gen 3, but then seeing all these different pokemon with new stat combos that work in direct contradiction to their type attack type. Not to mention the stupid amount of HMs you need to move about the map.
I try to replay Gen 4, but the available pokemon pre-e4 feels like such a small pool that I use the same team every time and get bored.
I try to replay Gen 5... and this one works pretty well actually, somehow Black and White AND Black2 and White2 are enjoyable experiences. I have little to comlpain about here.
I try to replay Gen 6... and I actually feel like I'm restricted to only looking for pokemon who can mega evolve, which cuts the options down to like 5% of the pokedex.
I try to replay Gen 7... and honestly, the cheesy nonstop dialogue just keeps me from playing the game so much that I struggle to keep motivation.
I try to replay Gen 8... Well... I'll be honest, I never finished Gen 8. After all this time, I'm finally admitting that pokemon just doesn't seem to work for me any more.