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Thanks for your help.  What about the unpaid gigs that were not considered charity?  These were for prearranged amounts but were never paid despite repeatedly billing. If there's somewhere it can be written off on his Sch C, the loss may provide a larger benefit to him than if he pursued this in court, If it's allowed, where would it be entered? Would it be limited to 2018 unpaid amounts? He had a few of these from the last quarter of 2017 that he was allowing more time to get settled before giving up and considering it a loss. Some were even earlier than that, like in 2016, but they kept telling him they would take care of it and just never did. Trying to keep up with hundreds of gigs every year makes it hard to continue revisiting the same people about the same issue, and eventually its just time to move on.