Comment by atrettel

Yes, you are right. In hindsight, what I viewed as "complicated" is not what everyone else views as complicated. Because I do this manually, I am much more aware of all of the different forms and roughly when to use them than most other people, so I don't view my taxes as particular complicated because I can see situations where they can get insanely more complicated. I filed more than just form 1040 with the IRS this year if anyone is curious.

As to the permutations aspect, this does take a lot of time but it can net a lot of savings. One thing that I would add is that you do have the choice to round to the cent or the whole dollar (at least with the IRS), but generally I have never found that to make any substantial difference, so I just round to whole dollars at this point and don't waste my time trying to optimize that.