Furry stuff, oekaki stuff, and other stuff.
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Yeah, both WP and OP are really designed to work from one place. Support for multiple boards and avatar paths has been hacked in, but not very well. The board has some simple replacements to keep paths from breaking, but nothing close to regex filtering and rewriting rules.
It's also worth noting that WP shares some paths for both local and relative paths, so I use "./" as a root path, and not "/". That's a bit safer, but not as flexible.
I noticed in setting up my board, that it doesn't cope with galleries being outside the oekaki path, or more specifically, all paths have to be relative to the install path.
When I set it up, I selected "/art/wp_draw" because I like to be able to refer to drawings in other places, and don't feel like digging down 5 layers to get to them. WP prepends "./" to all pathnames, so this ended up being ".//art/wp_draw" Since linux swallows extra slashes, this is equivalent to "./art/wp_draw/" which didn't exist. I changed the directory to "../art/wp_draw" and this resulted in "./../art/wp_draw/" which is a perfectly kosher (and real) pathname. I mainly noticed this because even though the pictures were showing, it wasn't generating thumbnails, which is interesting -- this means that gallery display is NOT using the same path as thumbnail generation (possibly a bug?). The Diagnostics tab showed the problem, and it was quickly sorted out.
Apropos of nothing in particular, but if other control-freaks are abusing their systems like I do, this might tell you what's going wrong.