I would clean up around the gear box and see if it is leaking. It sure looks like it is. If it is, I would drain all the oil out I could and then fill it with corn head grease. It will leak less when not in use but still provide the needed lubrication when being used.
If you have the time and knowledge remove the gear box an replace the seals. They are a simple gear case. The seals would be readily available by size. It would last you a life time then.
On the shear bolt. If you look the plates are thicker where the shear bolt is currently at. I would go 180 degrees and carefully drill a new square hole. Same size as the current one and use grade 2-3 bolts plus a lock nut. The thinner plates will wear out much faster if the bolt is allowed to loosen. Unless you are using it on a real big tractor you should rarely shear a bolt. I may have replaced one or two in ten years on mine. Those usually involves an ice chunk I should not have been blowing anyway.
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