For anyone having trouble with getting Leaderboard achievements for Road to Glory
The achievement guide doesn't state this, unless I read it wrong, but you need to actually play a game for the 3 achievements to pop up. I did the achievements by make a 99 overall LE for Idaho, simming 1 season and then simming all of the second season but the last game, which I played. After I played the game all 3 achievements unlocked. Not sure if this changed from when the guide was written.