Your jumping out of gear is not caused by the oil. The shift forks on your Cub are formed steel and bolt onto the shifting rods the shift lever move forward and backward. They come loose and don't completely move the the gears into full engagement. I think there's six short capscrews on the plate the shifter is attached to, remove those capscrews, carefully lift the shifter & plate and see if the shift forks are loose. Tighten the capscrews holding the forks if so.
You may have a bent fork too, or ground the gears into engagement too many times, or have a bearing or two getting worn and loose about ready to fall apart.
I've been around gear drive Cub Cadets for 55 years which uses the exact same components as your Cub.
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