I'm considering selling individual stocks that I've held with 2 companies in DRIP plans since the 90s (which have actually performed damned well over the last 20 years). I think I want to move this money into a nice index fund in a Roth bucket. I'm worried about the inevitable challenge that I've been putting off for a while: dealing with calculating capital gains tax on this.
Here's the deal: A family member set this up for me in the 90's as a set it and forget it way to deal with a small amount of savings I had when I was a kid. Since day 1 I have touched nothing, allowing the DRIP program to work. At the time, I was fairly ignorant and didn't keep good records, so I have absolutely no documentation prior to 2005 (thankfully, at least one of the companies gives me electronic access 10 years prior). As I understand it, I will have to calculate a cost basis to figure out capital gains, but everywhere I've looked for information basically says if you don't keep good records you're screwed.
Does anyone have experience with this? Is there any way to use estimated figures in a manner that jives well with the IRS?
Thanks in advance.