Duck, I would temper the enthusiasm a bit, although I know you sometimes find that difficult to do. Going to Tax Court is almost as painful as going to Superior Court. You’ll have to take time off from work and likely have to hire a tax attorney to help you. This is not traffic court.
You are not incorrect in many of your deductible items. Regarding deducting sales tax on gasoline, however, the IRS is clear that it is not deductible. Under the section of Taxes You Paid, it lists the following taxes as ones you cannot deduct: federal income and excise taxes; social security, Medicare, federal unemployment and railroad retirement taxes; customs duties; Federal estate and gift taxes; certain state and local taxes, including: tax on gasoline, car inspection fees, assessments for sidewalks, or other improvements to your property, tax you paid for someone else, and license fees (marriage, driver’s, dog, etc).
Regarding job related expenses, the IRS gives guidance as to what is deductible on Line 21 of Schedule A: safety equipment, small tools, and supplies needed for your job; uniforms required by your employer that are not suitable for ordinary wear; protective clothing required in your work such as hard hats, safety shoes and glasses; physical examinations required by your employer; dues to professional organizations and chambers of commerce; subscriptions to professional journals; fees to employment agencies and other costs to look for a new job in your present occupation, even if you not get a new job; certain business use of part of your home; and certain educational expenses. I would caution your haircut deduction.
For educational expenses, they can be listed on Form 1040, line 34 or go through the gyrations of the Hope Credit and /or Lifetime Learning Credit on Form 8863. Note that the Hope Credit is only for the first two years of schooling in an institution of higher learning. I doubt Johnny’s Flying Club to get your PPL falls under this criteria.
You yourself brought up the 2% rule. Depending on your AGI, it may or may not be difficult to overcome this rule. Everyone has to run the numbers themselves. Usually, what allows you to use the itemized deduction rather than the standard deduction is owning a home where you can deduct mortgage interest, points, and now mortgage insurance interest, as well as real estate taxes. Most of the other deductions are pretty much “chump change.”
Again, just so everyone knows – I am not a tax attorney, only an old legal aid lawyer who has gone to court (not tax court) with many members of the working poor who try to be a little too creative sometimes. Some things in life are worth doing, but many are not. Trying to game the system is one of the nots.