Stocks shouldn't be complicated; you've got a cost basis, a date of acquisition, a date of disposition and a final sale price. Withhold based on the deltas and you're all set right?
ESPP are complicated for me because my company withholds the taxes already, but that isn't reflected in the form I get from the stock company so I have to spend significant time every year refiguring out how to adjust and report everything while cursing myself for not taking notes the previous year.
