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I think good rule is to open external links to new windows and internal links to same window. I'm not sure if check box is done with php, I would suspect javascript and possibly AJAX, because it doesn't seem to reload page after checking or unchecking the box.

With Scribefire and WordPress you do uploading transparently, so it is quite good, but I haven't yet found perfect solution for updating my WP-blog. Usually I use WP's own dashboard for writing new blog posts, Scribefire is bit tacky for creating longer blog posts.