Need to drain oil, take cover off under PTO (slide drawbar out of way) and have a look. The bearings are tapered with a stake-nut to put load on them, just like a wheel bearing. Likely they are loose or failing - allowing shaft movement, which causes the seal to leak.
Make sure your bush-hog PTO telescopes freely under load. I had a round baler ruin my tractor PTO because it had a tight spot in it. It would telescope freely by hand but put torque to it and it wouldn't slide. Took me and a mechanic several hours to finally figure that one out!
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