Receipt or No Receipt for Repairs

[Alex Velez]

I own a three family house as my primary residence; I live in one of the units and rent the other two. Now, whenever I need a repair, I usually contact a handyman that I know; however, he is not a licensed contractor. Therefore, I pay him without getting a receipt because for 1.) he is not including it as income in his taxes and 2.) he charges me way less than hiring a licensed company. From a tax advantage perspective what do you think? What's the best move here? Thanks.

[John Underwood]

If you insist on using him.

You don't deduct these expenses.

Or 

You have him fill out a W-9 so you can send him a 1099 at the end of the year.

Any work that has unmanageable risk with it, you should get a licensed and insured professional to do the work. Otherwise you risk losing everything over one law suit.