Don't worry about the detail, or complexity, since it ultimately comes down to Muggins to manage.
The important thing in here is to stimulate some thoughts - if they're workable they'll be played with and influence the Categories, if not, they'll silently slip into the shadows.
I don't really want to critique individual items, but we don't have any geographic categorisation, and I'm not suggesting it be started (yet?), but the north, south, east, west is both too vague, and dependent on personal perception. Think of where English peeps think "The North" is!
The local government areas would probably do fine, but even their boundaries are a pain to find - get it wrong and I guarantee there would be a string of disgusted locals delivering virtual sackloads of complaints about having their assets stolen - well, maybe not, but you probably know what I mean.
I have to say I'm holding out for inspiration, and finding out some sort of easy, automated, way to put our point on a main map like I have on the ROC post page. However, as the data is in a completely different format, I don't see that coming soon. Maybe a long winter night project

I might add that the current categories were created as best guesses with nothing to guide them, some are good, some are bad, some will stay, some will go. For example, Gun Battery has gone (as an individual page category - it is now a top level category, and will change to Artillery Battery soon). Remains will probably be targeted next, since this can be implied for most items we report on. More useful, and likely to stay, is Lost, which is an important category as it contains sites that have been lost, are no use for visit (unless to disprove the categorisation) and are politically and culturally significant, especially if recently lost to development or lack of care.