Boolean Category Search Operations (in Menu if possible)

I’m building a website for a few teams to document apps, best practices, policy, etc. The 3 teams update or add pages at a rate of about 5-10 per week and there are about 200 total.

One of the problems with our current site is that adding or modifying a topic requires that we manually have to modify the code for our menus, ‘hot news’ areas, etc. I’ve decided to use wordpress as the base for doing the site revamp.

I believe we have settled on everything being a ‘post’ — and then noting the various categories that apply to that post.

We would like to be able to build the menu based on boolean combinations of these categories. For a basic example, a documentation post for an application might be in the categories “Windows” and “Apps”. This might show up in the menu item “Windows Apps” and another application might be in categories “Unix” and “Apps” which would show up in the menu item “unix apps”. Both items would show up in the menu item “Supported Applications” Further, if we wanted, we could create a menu item for “All things windows” … or whatever.

First, is there a way to do boolean category searches (then I could just do a ‘link’ menu item and it’d at least give me an accurate results page). Further, is there a way to have the results of the searches show up in the menu drop down?

Thank you for any nudges in the right direction you might be able to give me….