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1995 Yamaha 50HP oil leek

A friend of mine asked I had any idea what might be going on with an oil leak on his 1995 Yamaha Pro 50 tiller, and I don't. so thought worth elevating to the experts :)

It looks like oil coming out around the prop and around where the trim tab goes in. If he puts the motor in gear such that the prop rotates, more oil comes out than when in neutral. Thoughts on diagnosis and cost to fix?

Thanks!
 
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