I've installed a couple of windshields with the trim. Once on a '63 and once on a 69 or 70. I remember the older one being much more of a pain for some reason . . . I think it's the shape of the bottom of the windshield. Seems like the older glass has more of dip in the center that made it hard to keep the rubber on the glass while I was working the trim in place. It's been a few years, but I think what I ended up doing was putting the rubber on the glass and wrapping it with packing tape slightly off center. Then I worked the trim in one side, and wrapped tape around that side, cut the tape off the other side and worked the other half of the trim in and then the clips that cover the joints. From that point on, it's pretty much like the Cal-look rubber.
Everybody has their own tricks, but what I've found works best for me is to use a heavy monofiliment weed eater cord to install it. Wrap it in the groove twice around the windshield . . . that way if you have a spot that doesn't pull in quite right the first time around, you have a second shot at it. Don't laugh, but if you lubricate it with KY Jelly, it should pop right in place. (I know y'all can have a field day with that one . . . but the stuff WORKS!) When I put the windshield in Homer, I only lubed up the back side of the lip (the part you see from inside once it's installed) and a little on body where the seal sits . . . none in the groove or on the cord.