Understandable. My personal use cases for images fall into two categories:
- Short lived wikis for which file size is absolutely not a concern
- Wikis hosted on WebDAV where the uploader plugin automatically externalizes the images saving them on the filesystem.
@Scott_Sauyet that is pretty high up on the list for me as well. Ideally this needs to be paired with some sensible CSS class definitions that can be applied for different alignment and sizes.
If you use tiddlywiki on node.js there is a command that can do so. For single file wikis, the Upload plugin provides an option. It uploads any tiddlers matching a user specified filter to a backend, creating a canonical URI tiddler in its stead. Support for different backends is provided by uploader modules, which are pretty straight forward to write for RESTful APIs.
If TiddlyHost ever offers support for file uploads, it should be possible to write an uploader for it. You can convey your interest for this potential TiddlyHost feature here.
… and realized only afterwards that I had not moused-over to the check-mark to confirm that new name. 
Oh but wait, actually it’s time to load up a backup of my whole wiki, because that new image.png has just overwritten the image.png tiddler that still has that name from the last time I imported without remembering to mouse over to the checkbox to confirm my descriptive name… 
your tool drives me to further desires.