Tenant discount for lawncare?

[Matthew Lindsey]

Hi,

I'm nearing the end of my closing for my first 4 unit property (2 duplexes on one parcel). 3 of the units have tenants in place with MTM leases. I have a question that I feel like I know the correct answer to already but I would like opinions. One tenant is related to the current owner. The owner has given him a $100/month discount for him to keep the grass cut for both duplexes. The tenant uses his own equipment and has been doing this for 2 years. My question is does anyone else have experience with this sort of deal? I feel like letting this continue could be a huge liability on my part. For instance like slinging rocks into tenants cars, kids, etc. The benefit is that this is cheaper than hiring an actual business to cut the grass and I don't have to worry about writing more checks. On the other hand hiring a business should mean they would be licensed and insured. Also with letting the tenant do it I'm not sure if that counts as a expense(tax purposes). The tenant seems to be a good tenant as I have briefly spoken to him. If there is a surefire way to make this work id love to hear how to make it work and protect me as much as possible from unexpected expenses. Thanks for any input.