Hi Eddie, My apologies for the wait on this. With the release of recent updates, we're a bit backlogged. I don't think your dutiful tidying would have an affect here. When a GM deletes a game, Roll20 doesn't erase it from our servers. Instead its simply archived onto a storage server so it no longer hogs up your game list. So the games you've run from an account standpoint still exist. I've put together a bug ticket to see what our coders can figure out why the achievement isn't popping.