You will never develop your towing, backing skills until you attempt to do it in the most extreme circumstances! Remember, the strength of the crew is never demonstrated in calm waters, the real strength is demonstrated in the midst of the storm.
I hate 3 things, backing the trailer from the right, setting up camp in the rain, and backing at night. When all 3 happened at McCormick's Creek State Park in South Carolina last March, I almost gave up. It was so dark, so wet, I'd never been to the campground before, and we were very tired from traveling. My wife spotted me (pitch black night and trees everywhere). Looking over head for clearance, sides for trees, end of the camp site for more trees, missing the electric post, the campground campsite marker post, and the guy across the road who turned on his lights in front of me as if that would help me see better behind when all it did was blind me completely from the front!
But you know what? We did it. One inch at a time. Even though my wife was a great spotter, I got out of the truck at least 2 dozen times and went behind and check it all out, moved a couple more feet and checked again. And finally "in she went!" Success!
Am I a better "back-er-upper" now? Probably not! But, I know now I've got no fear of it.