How should I create my site map from the mess my previous SEO company left us with?

[CamiloSC]

This post is deleted!

[TomRayner]

I'd change the URLs and 301 redirect.

From a user experience point of view, you want to limit interruptions in the user journey as much as possible, so I'd redirect in that case.  I think your new site architecture looks neater - I'm also a fan of using hyphens and not underscores in URLs, for both SEO and user experience reasons - and so if I were you I'd move to that new URL structure.  If you do that, a 301 is imperative.

The new architecture makes sense from a UX point of view, a navigational point of view and even a crawler point of view, as there is a clear direction as to how users (and bots) should travel through the site.  I'd definitely go for it and 301 redirect the old URLs to their new equivalent ones.  If you have any pages left over with no new equivalent, try to send them to the most relevant category page.

Hope this helps.

[CamiloSC]

Thank you Tom for taking time to respond.

Your thoughts are exactly what I was considering (UX and crawlers)

I was second guessing myself having to change 95% of my URLs (using 301 of course) but this seems like the best logical solution.