Tax season again. Spent the whole day trying to figure out "cost basis" for ESPP shares that I bought in 2007 and sold in 2009. Naturally, it being 2010 now, I can't remember what I paid for the shares, what they were really worth, how much commission I paid, how much they sold for, what the price was at the start of the ESPP period, whether I already paid tax on the discount ... fuck it's a nightmare.
Also sold some BT shares that I bought at the height of the dotcom boom. since I bought them they split into two different companies and my broker got taken over twice. What records I have of the purchase are irrelevant, and the records eTrade has don't seem to match. Trying to calculate the cost basis on those took the rest of the afternoon! There's the price I paid for the BT ADR, then the price on the "BT PLC ADR" that they became after the O2 split, which doesn't seem to match the price eTrade has listed as the per unit share. Does that include the Dreyfus (or was it BrownCo?) commission? I can't tell.
It's not worth the hassle! But it was a tax write-off. Sometimes I think it might just be easier to keep all you assets as $20 bills in the mattress.