I have no statements for old stock purchases (done through reinvesting dividends) but I do have tax forms from 1988 showing that I had stock and have been able to figure out about how many shares I had (even though I know I bought some before that). So here is my question: by 1993 I owned 2000 shares of X stock. In 2016 I sold 850 shares and I can trace back that I would have sold some from 1988, 1989 and 1990. Now what? Do I just pick each amount (250 from 1988, 500 from 1989 and the rest from 1990) and how do you pick a date? I know on the tax form I got this year, it only goes back to 2005 and I have very specific amounts from then on. Is this something I should turn over to an accountant?
Sales of stock are treated (if you can't trace the purchases) are based on first in first out.
In your case, you would take the oldest ones (1988) first and work your way forward.
Good luck!