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Only problem is that every time I create a custom permalink structure I get back ERROR 404.
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What server are you on and do you have a htaccess file uploaded?
Mostly problems with permalinks can be caused by something going wrong with the htaccess file, so you might either need to create a fresh blank one or delete the one you have.
Alternatively some servers (Zeus, used by Netregistry, is THE biggest offender), need special mod_rewrite instructions to make custom permalinks work.
Any chance you could provide a link, or give more details?