Problem - How do I keep existing urls to a site to undergo redesign?

[monton]

I have this site that is more than 3 years old and has some decent rankings in the search engines for a wide variety of keywords. However, the site is designed very poorly as it was the first site I made when I was first starting out in webmastering and was done in WYSIWYG in Dreamweaver. What I did was to create several templates, one for each category and then uploaded articles using the relevant category and gave it their own urls using the title of the page.

However, what I would like to do now is to redesign the site in Wordpress. The last time I only used parent categories and then added articles, but now I would like to add several sub-categories assigned to each parent category so its easier for the user to navigate. But I would like to maintain the existing urls because it already has good amount of traffic.

So, my question is, how can I create subcategories and assign the existing articles to these subcategories rather than the parent category and still maintain the existing urls?

Also, since the site has around 500 or so pages, is there a way to import it without having to manually assign the articles to their respective subcategories or will they need to be done individually, in which case I am probably looking at week's work, not to mention the repetive nature of the task.

Any help appreciated. Thanks

[Cassidy]

There might be a better way, like outsourcing the import to wordpress, But I would create a subdomain with a wordpress site, and transition it page by page. You could use mod_rewrite to make it a seamless transition.

[monton]

There might be a better way, like outsourcing the import to wordpress, But I would create a subdomain with a wordpress site, and transition it page by page. You could use mod_rewrite to make it a seamless transition.

How would I therefore maintain the existing urls since I am going to want to change the structure of the way the articles are assigned to the actegories i.e. would like them to go into subcategories as opposed to parent category?

[Cassidy]

Sounds like a tedious task of laying out what the final result will be, as each page gets to the new temp site a 302 redirect, when you are done relocate from the temp subdomain to the main domain and set up 301 redirects.

[molona]

Hard to give an opinion about what would be the best way. My thoughts are that a mod_rewrite could do the job just fine. After all, its job is to create user friendly urls

If that's too complicated (if you are not used to regular expressions, as an example) you may want to do a redirect, as Cassidy suggests.

[Dan Schulz]

What server is the site being hosted on? Apache, or IIS?