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well if permissions are correct on the server there should be no unwanted files thats the immediate answer. I would begin to wonder if you persistently suffer from files not being deleted when we issue an unlink command in the script why this happens that is going to help you more than anything understanding why the server is not allowing it.
As far as cleaning up not much you can do except manually but classifieds is not hard unless your site is real busy. You can close your site for a few days or a week make sure your using your expire cron and then delete all ads till you get down to a point where you know only these are left and clean out files from the data directories except the few ads.
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