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Am I really expected to list all these to get to a total cost basis?

If you're selling it all, and.... if you're only selling a portion of your shares you list all the parts for that portion.

Also, if I reported the dividends based on each year's 1099, if I modify cost basis based on DRIP purchase, aren't I setting myself up to be taxed twice on those dividends?

I think I understand what you're asking. You shouldn't be taxed twice.
When you receive the dividend, it is taxed. The dividend then pays for the share. That is the cost basis for that share (or fractional share) when that share is bought. When you sell that share, you add or subtract the current value that you sold at, (depending if the share is higher or lower than when first purchased) if your basis was higher you get a tax benefit and if your basis is lower you just pay tax on that difference. Depending on how many shares you sell and at what price they were bought at, you may find some shares were sold below cost basis and some shares sold higher than the cost basis. You need to figure it out so you don't get overtaxed (or undertaxed, that's when the IRS can really be a pain.)

This is all only my opinion (and opinions are like elbows, everybody has one) based on my experience with DRIPs, as for the rest you really need to consult a Tax professional to make sure you fill out all the correct forms properly.
Using a good Tax software program can help too.

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