Hi Goatchay,
The pic of the plugs helps. I would have done the same as far as filling. If you look at where the shaft is and the lower small square plug is in relation to it, that plug likely would represent the lowest point that gear oil should drop to with use. The next plug up, the one you filled to would cover the gears and the bath/splash would also allow for expansion inside the gearcase withOUT blowing out any seals.
I was earlier suggesting the small square top plug might have been the vent plug, got lost and then was replaced with the standard square one now in place.
Or maybe your model never had a vent, just two small plugs?
For the split collar, I was thinking about clearances. If you could get a collar that was close to the overall diameter and wasn't too wide, a suitable sized thin washer sandwiched between the bearing outer race and the split collar could prevent the grass issue. This solution might depend on whether there is built in side to side play in the shaft. Since I suspect you do not plan to remove the shaft to do the bearing work, you might have to cut the thin washer and attach the pieces to the split collar, then move it into place against the bearing race.
BTW, Coyote Machine refers to my Kioti tractor, one of the best brands on Earth!

I am of course, familiar with the other type coyotes, they are less popular with most people. :confused3:
One other suggestion re the numerous pics- consider adding a brief description to what each pic represents or what you're trying to show us- unless completely obvious.