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  1. Snappy, I would also strongly suggest to your friend that he buy a book, or do some on-line research on self employment. As BRG said, there are lots of deductions available, some pretty obscure. There are also a few payments that are owed besides the basic income tax, like social security, self employment taxes, city taxes, etc lurking in the bushes to take your last dime. I don’t make a lot of money, compared to most here, but one of my best investments is my accountant, who has saved me from myself many times. I turbo taxed my returns a couple of years, and in my cheap ignorance, paid for it. Fortunately I didn’t own my home at the time, or I would have really screwed it up.