The drivers side is a bigger PIA than the passenger side for sure. When I put my tops up I keep the rear corners in their slots, pull the top up and over and then just start the front clamps, I don't tighten them the final click. I also do not put those two plastic clips in that go over the doors either, this gives you a bit more play room when getting the zipper started. I usually put my hip against the bottom of the window so it does not drop while starting the zipper. Also make sure the zipper is well lubricated, jeep sells a small bottle of lube with a squeeze brush applicator. No, you are not alone or imaging things. Just exercise care so you don't damage it. Oh, once I get about 1-2" of zipper started I put the plastic clips on the window into the surround slots behind the door. The very last thing I do is pull the front clips tight.