It’s a good idea when you don’t want to use the default structure 🙂
There are a lot (like really a lot..) of cases when site planning includes URL structure, it’s best to really have a grasp of this plan before you begin.
I would go as far as graphing out a representation of the relationships/slugs, that way you can compare it with the “default” structure to figure out if you can make an easy hack (hierarchy/hook) or you need something from scratch.
The http://codex.wordpress.org/Class_Reference/WP_Rewrite API is comprehesive and daunting at the same time.
I really recommend using CPT’s http://codex.wordpress.org/Function_Reference/register_post_type to create the custom structure instead of bending over the defualt posts/pages. It will make your life easier.
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