1099 and tax deductions
I often run into this situation where a handyman job exceeds $600 and therefore necessitates giving them a 1099. However, these people are not too excited to receive a 1099. Complicating matters further, if you hire an unlicensed professional for some odd jobs and they don't have an ITIN or SSN how do you all deduct these expenses on your schedule E taxes for investment properties?
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Really, you should be screening your contractors like you screen your tenants.
Do they have insurance? Get formal quotes. Get change orders in writing. Get a W4, and additionally insured before staring and a lien release before final pay.
The times I've had trouble with contractors is when I've deviated from best practices.