The park I acquired had a tenant getting free rent ($500) for mowing and leaf blowing. But no one was checking up on him. He liked to mow but when I got a property mgr to look things over he told him the leaf blower he had was a “toy” and get a real one to do the work since you are getting $500 a month. I checked prices of landscape companies and could get it done for $325/month. I switched.
In a way I could have asked this person to continue for less than $325/month (with a contract about being an independent contractor but that doesn’t solve the insurance questions), but then I’d need someone checking on him all the time. For my situation it seemed I would have better chance of it being done right with a company. So if you have your tenant’s help, have a way to double check that he’s really doing what you are requesting.