I’ve got to go with the hardest shot being a mid range chip shot out of the rough over a sand trap with not much green to work with. Almost impossible to get it close. I get cold sweats just thinking about it!
I don’t wear a glove when I putt. I have it on when I do everything else. Side question: do you take the glove off in between each shot? I do this because I feel it helps with the longevity of my gloves.