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Contributing an insurance deductible $1,000 will lower the taxable income on the $30,000 1 year person from $20,650 to $19,650 and save taxes of $150 (=15% of $1000). For the $100,000 per year person, his taxable income decreases from $90,650 to $89,650 and saves him $280 (=28% of $1000) - almost double the!

Defenders of this IRS position would say it comes home to Section 61. The waitress provided a service for me, and I paid hard. Compensation for services is taxable. End of story.

Now, I am hardly suggesting you exit and occupy a life in criminal activity. Tax issues would have been minor whenever compared with spending period in jail. Frankly, it just isn't worth it, but it's at least somewhat interesting and humorous notice how brand new uses tax laws to go to after illegal conduct.

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