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Is this the best way to do it, or is there a better way? Blog, or fed from a database?
How can I get key words into my content, when the content doesn't naturally have anything to do with any of my keywords. Obviously the content has topics that are very diverse.
How do the SE's read SSI's? Do they actually follow to the page that's included that day and read the content, or do they just read the SSI script.
Any help would be great!
Try putting 366 static pages together in a directory format which is linked to from the homepage. For example you may have a section of your menu that invites people to select a day other than the current one by linking to 12 'month' categories. The SE's will pick up the month pages which will link to all days in each month and, hey presto, you have a way to happily change your content on the dynamic pages without getting in the way of search engines.
Secondly, why not offer a free service which allows webmasters to add an 'on this day' box to their pages. All you would have to do is build a feed and make sure they link back to you. It could get you a few nice links.