This happened to me this week. The hub I turned around in had my set stacked up for me. When I went back to hook up, that was the hose for my front box. It was cut completely, so I couldn't even hook up and drag it to the shop. I had take the front trailer to the shop and leave the dolly and back box behind.
To add insult to injury, when I got back, some dirt bag stole my dolly.
I couldn't blame the spotter, because when I back up a trailer to a dolly, I tap the dolly with the front box, then pull up a few inches so I basically only have to lift the dolly straight up, onto the hitch.
To me, it's more convenient. Anyone who has tried to move a dolly more than few feet on gravel, snow, ice or a gap in concrete knows what I'm saying.
The only difference is when I set everything up myself, I check the hose on the front box to make sure it is behind the hitch pin. Then I check the hose on the dolly and make sure it is tucked in the hole behind the eye and not wrapped around the front of the dolly. Then I'm good to go. (If I think of it, I'll post pictures of that too.)
You're always trying to avoid pinch points with the hoses.