I liquidated a couple managed-asset accounts last year, each of which held between fifty and a hundred different stocks, thereby creating almost two hundred taxable stock sale events on my 1099B forms—all of which had to be entered into the TaxCut Pro software I used.

To make matters worse, I switched investment firms last year, and while the aforementioned accounts did get transferred, all the cost and purchase date information—how much I paid for each stock and when I bought it—somehow got lost in the process. Consequently, a couple tedious hours of data entry became a dozen hours of forensic excavation through a year’s worth of transaction records and account statements.

And finally, to add insult to injury, according to TaxCut Pro I can’t file my taxes electronically because “the IRS doesn’t accept returns with more than 97 capital gain transactions”. Funny, I must have been crazy to think that the point of using computers was to reduce paperwork…

So, what we have is information that was in Merrill Lynch’s computers, got printed and sent to me on paper, got re-entered into the TaxCut software, will get printed out again as my tax return, only to be re-entered by some unfortunate cog slaving away in the bowels of the IRS. The pointlessness and stupidity of it all never fails to astound.