NOTE: You can play on rookie mode and set the GM difficulty to rookie mode.
Edit the rosters and take all the best NHL players and put them on one team. Then make sure you set the playoffs to “Single Game Elimination.” Now all you have to do is keep on simulating. You don’t have to worry about trading players, or anything like that. Just try and resign your players if their contract expires and make sure you win the Stanley Cup every season. Soon after your 3rd Stanley Cup season, you should have enough GM points to unlock you legend plaque. Manually save after each playoff game encase you lose.