That's why we leave the dupe detector so porous. HN's goal isn't to build a database of unique urls—it's to have the most interesting front page possible.
This system is easy to abuse, so we ask people not to abuse it. For example, don't delete things and then repost them. But I don't see abusive reposting as a huge problem on HN right now. We catch most of it, and alert users catch nearly all the rest.
Edit: I should mention that we're going to be releasing a new approach to /newest that addresses the tendency of good stories to lose their chance at the front page too quickly. Exactly when we release it depends on how much code I get to write in the next month or two.