Stock options are definitely complicated, but so are your taxes. In fact, your taxes are much more complicated. However, there exist reasonably good software to

Stock options are definitely complicated, but so are your taxes. In fact, your taxes are much more complicated. However, there exist reasonably good software tools, eg TurboTax, to represent your taxes as a decision tree, and to walk you through it. The problem isn't really that stock options are complex -- it's that there doesn't exist comparably good software for stock options. I'm actually building software to solve this: http://www.optionvalue.io http://www.optionvalue.io. Right now it covers value in exit scenarios, but am currently building out exercise / tax scenarios.