Never had to take or structure a deduction in a manner that wouldn't cause a competent accountant to take a long time to explain(without any prior involvement), involve jurisdictional games, nor would rely on untested territory of the tax code. I don't make a point of having my tax forms hit the proverbial hornets nest of Federal, State, and City revenue collections.
If you're suggesting that taking a simple deduction on one's 1040 and receiving a negative sum or a lowered positive sum is the same league as things like Double Dutch, you would be mistaken. That's like asking an amateur in a sport being taken in at the professional level and thinking they won't get outclassed.