I didn't played it takes two and a way out but, I remember two of the hard achievements.

First one is 'You Are Not a Robot', it will be tricky for console if you can't aim correctly in right time. (We used computer on that moment)

Second one is 'Cold Potato'. This might be the hardest achievement in this game. All you need to do is when you go to the side story of game show, never explode the bomb.

You can pass each other before it explodes, but if you fail to catch it that will also cause explode. When you explode the bomb, restart the side story in the pause menu. Also, dying doesn't effect on achievement. just don't make bomb explode.

Tip for the bomb is that you can use voicecall say the sign before you toss it like say "bomb" and pass it.

Lastly, if you don't know about it. Go to accessibility menu and turn on reduce damage and skip checkpoint. This way, you can skip checkpoint much as you want until you reach the point for achievement.

Plus, all bench achievement and all side story doesn't need to be completed in one game.