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>>>>For the benefit of someone not currently in a DRIP program but thinking quite seriously about it, could someone please enumerate for me the "administrative" headaches involved? Do these simply arise from having to track multiple purchases over time at multiple different share prices (i.e. for tax purposes upon redemption) or are there other factors?<<<<

You call up the Company and request an enrollment form. You purchase the stock through a broker and tell them that you want the certificate mailed to you (about a three week process). You then mail in the certificate with the enrollment form. Check the box full dividend reinvestment.

You're done! They mail you a statement with a purchase coupon attached after each purchase in order to confirm your most recent purchase and also to facilitate your next one. After a quarterly dividend is reinvested you get a cumulative statement showing the current year activity. To sell takes a few days (one disadvantage). Your paperwork will consist of the last cumulative statement of each year. When you sell you can pick off the costs from these statements to the extent of the number of shares sold. Compared to stocks purchased through a broker it's more paperwork, but it's really not that bad. This is especially true after the initial setup. (It's in fact better than any mutual fund especially when considering all the brochures and solicitations the funds send you.) Sales aren't frequent enough to be a factor. Afterall, you really shouldn't be purchasing in a DRiP a stock you plan on trading often.
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