This doesn't solve your whole issue, but you can quite easily get rid of
one step:
As of now, one goes to import on the page toolbar > import's an image as a
> tiddler > changes the title of the image > transcludes the image-tiddler
> into the tiddler one wants the image to be in.
>
If I understand correctly, your students must transclude their image into
one well defined and preexisting tiddler (in the toc). If you have a
one-one tiddler-image relation, what if you prepare this transclusion for
them, for example with {{tiddlername.jpg}} or [img[tiddlername.jpg]], and
they only have to rename their image (it is already in the process)
accordingly "tiddlername.jpg"? Or, if there may be more than one image per
tiddler, you could use a list to transclude all the results of a prefix
filter (except the tiddler itself, for example:
[prefix[tiddlername]![tiddlername]]).
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