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When I started my site it was poorly organized. When I went from static HTML to a CMS, I pretty much had to reorganize. At the time I didn't know how to use .htaccess and 301's, but it was pretty easy to learn and I was able to use some simple regular expressions to dramatically cut down on the number of lines of rewrites that I needed. The Apache forum here [webmasterworld.com] is an excellent resource to get the help that you might need.