Weirfan if it were me I’d ask the short strap guy if it was uncomfortable. When I caddied, once in a while we’d “short step” the other caddies bag when we carried it out to the forecaddie spot while he tended the pin. I remember you’d pick up the back and be like “wtf!!!” And the other caddy would laugh.
The handle thing…. I dunno. My father who rarely played, and was awful carried it that way. I used to tell him not to. He said it was easier because he had to put it down every 10 feet😂🙄.
A kid in a league here was going off the first hole and I knew he was new. I actually went out as he left the tee and stopped him and said, “ you’ll never make it 9 holes carrying the bag like that. I fixed the strap, and showed him how to carry it. In the process of me getting a knot, yes a knot out of the strap, he leaned over and my hand slipped and I punched him in the face by accident.
There’s a reason tour caddies don’t carry bags like that. And it has nothing to do with being on tour.