playing it with someone who hates losing and gets really angry
What is the hardest thing in chess???

But secretly I suspect that winning a lost position is even harder.

no one said winning yet?
Winning for me. Also Making draws. In my entire life I have made only 1 legal draw.
The longest chess game is 269 moves between Ivan Nikolic vs. Goran Arsovic, Belgrade, 1989. The game ended in a draw. The game lasted over 20 hours. Nikiloik and Arsovic clearly had no such problem. Even after 269 moves no one really won. It was a draw. It should have been a draw earlier. There was 3-move-repitition but no declared draw.
Trying to get the opponent to not abort or abandon the game.
And, Trying to not stalemate with a queen up
waiting for opponent to play, and have a boring position. I prefer to resign.