Set up a pulley
Hi---I have rope and pole awnings for both my trailers, and find that they are awesome in all weather situations, as long as you have heavy duty springs, and heavy duty pegs!
People swear by their "zip-dees", but when we were in Nova Scotia and Cape Breton a few years back, we noticed that those folks hardly ever used them because of the wind.
I have to agree with you that setting up the awning for the overlander is a pain in the butt, unless you have two people. I had a loop sewn onto the top ends of the awning, and tie a rope to it. That way, I can stand on a step ladder, feed the awning into the rail, then get off, pull the awning along by the rope, and then repeat the process. With two people it takes about 3 minutes. By yourself, about 10-15.
I bought a small pulley a few years back, planning to attach it near the far end of the awning rail, so I could just stand on the ladder.....feed, then pull, feed, then pull, etc. I never think to install it while I am home, so it hasn't happened, but I believe that it would work very well.
I plan to take my small awning on trips when I am by myself in the big trailer, and changing campgrounds often, as that is a cinch to set up!!