I finally got it all torn apart, and found a couple issues. The front rub block on the door side was not there at all, and the front plastic button on the glass was actually the one intended for the rear. I think the absence of the rub block combined with the extra thickness of the wrong plastic button was causing it to catch on the lip of the door skin before it was all the way up. I got all the correct parts rounded up, hopefully, it will solve the problem.