tax document hall of shame

And even for those who don't have to calculate the above, Etrade's "help" in getting you a basis for capital gains/losses is absurd: a list of what you happened to buy the same year. Not anything earlier (except online which is a "little" longer"), and even when the list is useable it doesn't match together common sized parts of a trade and often requires excruciating recalculation. And could they bother to put a meaningful ticker as an ID?

A single 10 share buy order may execute in 3, then 7 shares at different prices. A sell order may execute in 8, then 2 shares at different prices. This crosscuts into up to 4 categories that fidelity handles transparently, but in etrade you have to painfully finesse them out. Don't chide me about how some may want to FIFO vs whatever... automatically handling it in (any) default mode is the top priority.

The basic is to keep your own records accurately. Some group all transactions in one equity together in a schedule derived from chronological records, for example. Some prefer a database, carefully contructed so any relevant data can be extracted. Spreadsheets are probably easier, unless you have huge volume, and spreadsheets are more versatile as far as calculations such as rates of return on each position. Brokers do not necessarily account for accrued interest, nor for dividends or distributions late in the year not actually received until the start of the next year.

I meant you have to add the dozen monthly distribs for each of the funds with gov't obligations (so maybe a dozen times a dozen). Furthermore I am pointing out needless examples, that are avoided by typical industry practices.

Speaking about bad tax human factors, be sure to not skip a year logging on to your eftps.gov account. Even if you aren't going to use them to xfer funds this time, they apparently expire your password with disuse, and you can imagine the excruciating hurdles the .gov mentality puts in front of you to get it reset.

This shame award may be for something unavoidable, but a major brokerage sends out a corrected tax form "unqualifying" a boatload of dividends. The timing is the issue; it comes instantly after the deadline that it's sponsored tax software insisted you finish submitting taxes before a price rise (to penalize last minute filers).

BTW this sponsored tax software, previously offered free, now pops up with a gargantuan charge and will get it due to creeping commitments of tracking carryovers, etc. And I have learned how to answer it's annoyingly imprecise questions with counterintuitive answers that make it treat things correctly. Ugh, I am rewarding bad behavior.