You might want to check your .htaccess file. Whenever I get a 500 error that's the first place I look. Recently, there have been instances when we upload an image or change something in the page SEO area (using Yoast's SEO plugin) and when the page is saved, the .htaccess gets nuked. Whether this is a WP issue or an issue with our hosts remains to be seen. Media Temple & Rackspace Cloud are where we have seen these kinds of issues.
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