I doubt any court of law would find you legally liable for the cost to repair his equipment (unless you intentionally and knowingly set him up for damages which is hard to establish), since he's doing it for hire he assumes the risk for damage to his equipment, it sort of goes with the territory that if youre plowing snow and you cant see all the obstacles theres an inherent risk of hitting something such as that stump.
HOWEVER if you feel that morally your not warning him of the stump contributed to the damages and it bears on your mind theres no harm in offering to pay at least part of the repair cost.
You might consdider just asking him about it to avoid future hard feelings, I think I would.
NOTE I do not see this really as a legal question, its just a moral issue between you and him and your own conscious.
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