Attorney’s fees to produce taxable income are deductible. Since part of the disability payments is included in gross income, part of the attorney’s fees is deductible. However, you treat them as a miscellaneous itemized deduction, which means:
You’ll have to run the numbers to see whether you actually get any tax benefit from deducting attorney’s fees.
For calendar year 2007, taxpayers covered by an HDHP may contribute up to the lesser of the annual deductible or $2,850 ($5,650 for family coverage).