I don’t have any trouble getting the leading edge of the film into the opening groove of the reel. I do the same thing as you. I slip one corner of the film into the groove, hold it, and then slip the opposite corner of the film into the opposite groove. Then I push the film in about 2-3 inches until I can grab it in the recessed wedge.
The problem is after that. I try to gently load the film onto the reel, and it will move smoothly for 2-3 inches. But then it will jam. And I have to back it off an inch, and try again. And the further on the reel the film advances, the more difficult it becomes to load! To the point when, if I’m trying to load two rolls, the first roll becomes almost impossible unless I “force” it. And yes, this is with a bone-dry reel.