1) To make obtaining this and all other achievements faster go to options and turn speed play on
2) Custom play -> Rainbow -> Two players -> select location (no need to change default location)
3) Select human for player 2
4) With player 1 (you) roll dices once and select square with most points.
5) With player 2 roll dices once and select square with “-“ mark or lowest points.
6) Continue until you finish the game and you can start new one right away.
Starting from Custom Play menu it takes about 1min 50sec until you are back in Custom Play menu and ready for another game. I think you can make it in 1min 30sec if you really focus and just select point squares for P1 no matter what points it has.
Same method works for all these achievements, you just need to change game mode:
Classic master
Duplicate master
Classic Sensei
Rainbow sensei
Duplicate sensei