How can I create a permalink with two categories, with the order based on the parent category?

David, welcome to wordpress answers. The answer is: Switch to some other platform. WordPress can not with what’s currently in core produce such a result easily.

Technically spoken it’s possible, but folks hate me here to say how (well Apache + PHP) in concrete, so I don’t tell it because I fear the negative karma this give on this site.

Just switch to something else if you seriously want to do such stuff and more. Like symfony2 with a database layer. After about one to three month as a single developer you can achieve much more then you can imagine with wordpress.

And the best thing is: You can even add a wordpress blog later on. 😉