Stupid question but could be a factor...

You get used to it. Notice I said "get used to it". Nobody likes it but sometimes it goes with the job.
The way a guy hangs his chains on the rack has a lot to do with how easy or hard the job can be. If you hang them right they'll peel off with no twists and tangles and be in the right position to just grab and throw over the duals.
Still ain't fun, though. Especially that last one of the day.
My personal best was chaining eight times in one very long day. We were shuttling logs from a landing in the woods to a reload a few miles down the highway from the haul road. The highway was bare, we chained to get in and out of the woods on the haul road.

 

Very familiar with the road.

 

Well sort of....have seen slush, snow and Ice on the those roads.

 

One set of Three railers on the drives, set of singles on the trailer, about 20 minutes

 

There are so many things about trucking that has changed or is in the middle of changing. As i said earlier I only chained up so I could get to a legal parking place. With these smartphone apps and the internet technology has totally changed how truckers get their information. 30 years ago someone headed west on I 80 would not know that the mountain was closed unless they caught a sign or heard it on the CB pretty much until they got up there. This has changed. Back when I was running sometimes my FM would send me short messages about weather conditions. Because of this most drivers will know about those flashing signs in enough time to get stopped. However even in the face of this. I still think a driver needs to know how to chain up. While it sounds easy in some situations it is NOT. The last place you want to be out messing around trying to figure out how to chain is when it is 25 degrees out and the wind is blowing. I can tell you from bitter experience this is a bad time to be learning.