There's no need to do all that heavy accounting and itemizing. The IRS has at least a little common sense, and allows you to state "various" for the dates of acquisition, and report the sum total of the acquisition cost "basis" (although you still have to distinguish long term vs. short term holdings). See page 65 of Publication 550 ( http://www.irs.gov/pub/irs-pdf/p550.pdf) and the accompanying example.
So for anything held more than a year, all you have to come up with is the total of your purchase price (plus any reinvested dividends), which should be much easier to establish than all the individual purchases and dates. The reinvested dividends might be more painful to locate, but if you don't mind making an extra contribution to Uncle Sam, you can even choose to ignore those records -- you've presumably already paid taxes on the dividends; reporting them adds to your basis, lowering your current tax bill, so if you ignore them, you essentially pay taxes on the dividends twice -- but depending on the amount of the dividends and your situation, it might be less hassle.
Once upon a time it was expensive to buy stocks. Brokers charged retail commissions of several percent (really!) and charged extra fees on top of these for odd lots (less than 100 shares).
In the 70's there was a revolution wherein a new class of brokers called "discount brokers" appeared. These guys evolved and took over a huge chunk of the brokerage business.
DRIPs were created to get around the big broker commission problem -- a problem that no longer exists. Maybe in the 80's they were still useful to a significant fraction of the public. But now?
The discount brokers have lowered commissions until the commissions are so close to zero that they are hard to measure. Much smaller investors can now just buy stocks without resorting to DRIPs.
