I would go out on a limb for the kid,not many people give them opportunities to make something they can be proud of .most want to push them off to fast food .I have had 16 yr old sub stuff from me and as far as insurance goes, I have talked with them and explained the importance. If they are still onboard talk to insurance company and see what percentage it raises your insurance , then explain to them that this is the percentage that the insurance will cost and deduct it from the pay as insurance. They can then still write it off as a tax deduction. That makes it a win win situation You have a sub that if all works out can work with you on mowing side and he has built a reputation and business he can call his own to be proud of . Not many youth have the chance or want to .