As suggested, besides the bolt coming lose, you need to make sure that the slipper clutch is properly adjusted. It is there to protect the driveline, and if it is set too tight, or if corrosion is adhering the clutch surface to the plate, it can't do it's job. I don't know about your cutter, but my KK tiller manual suggests to loosen the bolts on the clutch every year before getting ready to use, and make sure it can slip. I've learned, in that application, that 9 ft lbs of torque on the bolts was sufficient to allow the tiller to function and still slip when necessary.
On a side note, I believe that the strength rating on a grade 8 bolt is based on pull, not side load. While I'm sure that a grade 8 bolt is harder to shear than a lighter grade, there isn't a direct connect to the rating when used as a shear pin. I seriously doubt that a grade 8 bolt (depending on diameter, of course) would be stronger than the driveline/gearbox. I'm not advocating using a grade 8 bolt in place of a proper shear pin, just commenting on the concern for the gearbox.