Matt, I agree with bagi with 100% conviction. BUT with the following caveat, you do NOT have to do it for all pages!
This is what I suggest you do.
1. Check your backlinks PROPERLY, using yahoo, altavista, MSn & Google webmaster tools.
2. Identify your deep links (links pointing to inner pages)
3. Identify which pages are ranking for terms that bring in traffic (using your server logs)
4. Identify pages that are getting traffic landing on them regularly (this could be from emails, virals, pages on forums that are members only, popular bookmarked pages etc.
5. Identify corresponding new pages for the above pages
6. Set up 301 redirects in the htaccess for the affected pages.
What you will have then achieved is to ensure that you do not send existing traffic to a lost page, therefor maximising it. You will also have told google which of your pages have moved, and which are no longer in existence. the new sitemap will mop up everything else!
There is a simpler option however, in as much as you could set up a 301 redirect match between the two structures so that any request for one url string will be forwarded to the new url string.
One last question,
Where shall I send the invoice for this high quality advice LOL
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