Four hopefully helpful comments about you PTO shaft.
1) Make sure both the tractor shaft external and PTO shaft internal splines are clean and have no really sharp edges. Then put some type of lubricant on both. I use grease, others use oils.
2) Use some type or rope/bungee/spring to hold the weight of the PTO shaft up. Can be supported from the mower or the tractor, just has to be out of the area you need to be in. AND remove it after you get everything hooked up.
3) Learn how to disconnect the plastic shield and slide it back out of your way to provide you better access and sight line.
4) Rotate the mower PTO shaft. May need a bar or screwdriver though the yoke to move and stop it???