First he needs a home office. Use all available deductions associated with it—utilities, car, insurance, etc. Also he should take maximum SEP IRA deduction. This will greatly reduce the taxable income associated with his self-employment.
He needs a house with a big mortgage payment to reduce his taxable income. If he has some savings, I suggest hiring an investment advisor. The 2% management fee adds up and will further reduce his taxable income while hopefully growing his nest egg.
He can also give to charity and take advantage of other Schedule A deductions.
All of this assumes that the Obama soak-the-rich plan kicks in if you have 250K left AFTER deductions.
Home office? Not the best deduction. It can flag you for an audit and affect your taxes when you sell your home.
Anybody making 200k or more should have an accountant.