Do I have to pay taxes - property manager / handyman?

[Jeremy T.]

One of my tenants is handy with repairs and I have used him to fix issues in units and turn around units to rent-ready. I claim a deduction for the material expenses which I buy at the store, but the labor I just write off as a personal expense and don't claim a deduction.

I am assuming that because I don't claim a deduction for the labor that I don't need to ask my handyman and sometimes informal property manager to fill out a W-9 which he is reluctant to do.

Thanks in advance for any tips.