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2. Yes.
Getting the comments is another step, as they're in the wp_comments table, and are linked with a comment_post_ID field. If you know a little mysql you could extract it fairly easy, and also if you know some PHP you can write a query that would bring it all out in a nice human-readable format.
(Pretty simple code to write, if you're not a coder)
2) There are services that will turn your blog into a book (blurb.com), or you can use the wordpress export feature to get your posts into an XML file.
Kristin's idea to use the WP export feature is probably you easiest bet; once you've exported all of your content to an XML file you can crack it open on Word (or the editor of your choice) and go crazy with formatting and searching. If that doesn't work for you though I'd be happy to help you find a workaround.