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

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You can accomplish even better than the capital gains rate if, instead of selling, you just do a cash-out re-finance. The proceeds are tax-free! By the time you determine taxes and selling costs, you could come out better by re-financing extra cash inside your pocket than if you sold it outright, plus you still own the house or property and in order to benefit by way of income on face value!