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 2007, a high deductible health plan is a health plan with an annual deductible that is not less than $1,100 for self-only coverage or $2,200 for family coverage, and with annual out-of-pocket expenses that do not exceed $5,600 or $11,200, respectively.