Spray some penetrating oil on the output shaft. There might a be a small hole
on the spring side of the yoke pin. Put P-oil in the hole and in from the pin side as well. You could pry LIGHTLY between the tractor and the yoke.
You might be pushing the pin in too far? Instead of pushing the pin in flush, let it protrude 1/8th of an inch. Finding the groove in the pin is a little bit of trial and error. I would guess this is your problem.
Once you get it apart, do a through job of cleaning the output shaft and the internal splines of the yoke. Use a skinny screwdriver to scrape the grooves.
Put a light coat of grease on both parts.