Tags
Sure I have something like a hundred sample characters published on the site and indexed on a single page. But with over 200 maps now on the site, a raw chronological index of the maps just isn’t cutting it anymore (at least, from my side of the monitor… and according to a few friends on google+).
I’ve already taken the first step of putting the urban maps on their own page, but I really should get around to indexing the other maps I’ve drawn over the past four+ years of blogging.
What map headings/categories would be useful to you?
Dyson's Dodecahedron 
Sizes. Microdungeons, minidungeons, normal ol’ dungeons …
I think a bigger question for you is, how much of your focus do you want to devote to creating and managing a fully indexed and categorized map archive? I mention this because asking for public opinion on map categories potentially opens the door to an involved process of cross-indexing all your maps in a complex manner. Perhaps rather than trying to create the perfect set of categorized map pages, you may be better served by tagging all your maps with various terms and creating a page allowing people to filter listings of your maps by certain tagged criteria. For example, someone may be interested in a map of a village with a ruined tower with an entrance to a dungeon. Selecting “town”, “ruins”, “tower”, and “dungeon entrance” would result in a (short) list of the existing maps with all those tags.
The advantages of this method are numerous, most importantly though is the boon of not needing to create (and maintain) a potentially growing set of map category pages. You already have the ability to tag your posts, so it is really only another way of displaying what your blog is already doing for you. This automates such tasks as making sure all your “town” maps are included on a specific page. Also, since this method relies on tags, it is extendable without requiring revision of what is previously done. If in future you were to create maps of say, buried alien spacecraft combined with fantasy style dungeons, all you need is add a tag like “spacecraft” to these new maps and everything trundles along without a hitch. If you decide to denote which of your maps are supposed to be near or within a mountain, you can create a “mountain” tag and add it to all new AND old maps involving mountains and nothing else need be changed.
Agreed.
The problem is that the way this theme works, at least, is that the list of articles you get from viewing a tag doesn’t actually show the map until you click on the article…
I might have to switch to a hosted wordpress install so I could use additional software and plugins to make it work purely from the tags.
I’d second that!!!
Tags for content would be a load easier for you and I’m betting the navigation toolbar would flow smoother too.
For me, I’d like to filter by Natural Cavern, Man-Made, Surface Structures and things like that. The size doesn’t really matter, but the environs do.
My suggestion: Migrate your WordPress hosting to a paid solution so that you can use plugins. I’d then use something like Nextgen Gallery to display all of your maps on a gallery page. Finally, install Nextgen Powertags so that a user can filter the gallery tags that you assign. That way you don’t have to maintain anything special, just one or two descriptive tags on each map post.