Hahaha... This is a long shot, perhaps.
It's both a question of "How might one try this differently?" and... would Elliquiy have some (practical) use for it being done differently? Or... am I not aware of [insert already cool site-friendly thing that can work with this sort of stuff]? This might be more relevant to Group Games (or small games) that somehow utilize World Building creations. I am trying to think of a relatively 'simple' way of adding a visual aid to players... and get a perspective from others more experienced with this. The initial question, though...
Could one create an image (like, a political world map) that could be changed (directly or... ?) in some "simple" way (region colors, for example) based on changing situations in a given story? The only way I can imagine it would be changing the image and reuploading it to the Wiki to replace the outdated picture. But hey, two heads are better than one. Maybe others could be more inventive than I. Another reason I ask this is perhaps due to a pre-emptive guilt complex when uploading images to the site. Heh... Like I might be afraid of being too much of a nuisance on the server with a bunch of reuploads or something. Combine that with this OCD of trimming the fat on what I upload to begin with. I might just be too worried, but part of this half-baked idea(?) seems like it could be useful? If there was a way to pull it off, that is.

Is it okay to delete one's old pictures while replacing/reuploading them, or... does that cause other problems? I clearly haven't uploaded in a while... so it couldn't hurt me to be
conscious of that, at least.
Also, I apologize if this is confusing... it's still early and I might be overthinking this from too many angles. If this is confusing, I will try to make this a bit clearer. It is actually several similar questions at once, so I apologize.

Thanks for your time!
-Dall