Categories and automatic generation of URLs

howdy!!

I’m using intending on using WordPress as a CMS to replace the Joomla CMS currently used on http://www.shackn.com . I’ve selected WordPress because it is far superior when it comes to SEO and content manageability.

I’m trying to work out how to set up the categories, which in turn, will generate the URL structure I require.

The articles contained within WordPress will fall under 3 categories.

• Surfbreaks
• Accommodation
• Overview

Each of the above categories must also be associated with a physical location, either a town, region, state, or country.

The site will cover Australia for starters, and then expand to include other countries in the future.

Rules & Logic
1. Each town will have one or several surfbreaks attributed to it
2. Each town, region, state and country will have an overview
3. Each accommodation will be attributed to a surfbreak
4. Surfbreak URLs should look like this http://www.shackn.com/surfbreaks/australia/queensland/goldcoast/kirra/kirrapoint
5. If a Surfbreak URL is chopped back a (e.g. http://www.shackn.com/surfbreaks/australia/queensland/) all relevant records for that location will be displayed, in this case, it would be all surfbreaks in Queensland
6. Accommodation URLs should look like this http://www.shackn.com/accommodation/australia/queensland/goldcoast/kirra/paradiseresortandspa
7. If an accommodation URL is chopped back a (e.g. http://www.shackn.com/accommodation/australia/queensland/) all relevant records for that location will be displayed, in this case, it would be all accommodation in Queensland
8. Every individual location (whether it is a state, region or suburb) will have an overview. The URL for this will look like http://www.shackn.com/australia/newsouthwales/sydneyeast/overview or http://www.shackn.com/australia/overview
9. On the post or page for each individual surfbreak, I would like to be able to also display the recommended accommodation for this surf break. And vice versa on for each individual accommodation surfbreak

(This is all currently functionality on the existing http://www.shackn.com site, except for the URLs stipulated above, so if it doesn’t make sense maybe visiting the site itself might give you some more context)

So for the categories, do you think the best way to set them up is as follows:

Proposed Categories:
Surfbreaks
Accommodation
Overview
Australia
-New South Wales
–Sydney East
—Cronulla
—Bondi Beach
–Central Coast
—Avoca
—Gosford
-Queensland
–Gold Coast
—Surfers Paradise
—Kirra
—Burleigh Heads
–Sunshine Coast
—Noosa
etc

If I used these categories above, how would I attribute an accommodation to a surfbreak? Maybe some sort of “Related Posts” plugin or something?

Also, if I use these categories above, how do I get the URL structure that I have mentioned above??

Finally, should I be using pages or posts for each individual article?

Thanks so much for your time, apologies for the long-winded question…