Letting handyman live rent free if he maintaines multi properties

[Marquis W.]

I had a guy that I have been using to fix my properties here and there offer to take care of all of them (which is 4 properties as of now but will be adding 2 more soon) if I let him live in one of them for free? I would still buy supplies but labor would be in exchange for him living in my rental which if i did it would be the least income producing one it rents for $500. Anybody every did this and how did it work out for you? If I don't receive rent from this property I will still be in the green across the board  but barley. If one of the other properties became vacant then I would be in the red. I could easily find enough work for him to do to justify the lost of rent but is this smart?