Mark Glaser at OJR has an interesting article on "The good, bad and ugly of contextual ads".
Among other things, the article points out that infrequent crawling can lead to problems where advertising is targeted to content that is no longer on the page. The problem is even worse for personalized sites, since the pages the crawler sees may be nothing like the pages each reader sees.
See also my previous post, "Personalized advertising on Findory".
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