When an asset that is marked as “should be published” is modified, it should be displayed differently in the left nav until it is published again. This way it is easier to keep track of which assets are “dirty”; and by “dirty” i mean that the last modified time > last published time.
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1) It would need to keep track of environments (e.g. this page has been published to "test" but not "production")
2) It would need to know not only when the page itself was edited, but any of the blocks/XSLTs that changed the page's rendered content.