If I wanted to add functionality to lists: (unordered lists)
I.E. edit, dragsort, delete
I am thinking I should start with expanding config.macros.list.handler

The list macro is quite different from the list formatter:
    http://tiddlywiki.org/wiki/List_(macro)
That is, the former generates a list of tiddlers while the latter converts wiki markup ("* foo") to HTML ("<li>foo</li>").

If you want any list within a tiddler to be sortable, you might have to hijack a function like displayTiddler, modifying any UL/OL/DL after they have been generated. Or you could use event delegation, e.g. globally tracking click events, detecting double-clicks on list elements which then activates edit mode. (I assume you already know about jQuery UI's sortable and draggable?)
Note that persisting (saving) changes might be a challenge in itself.

Finally has anyone else ventured into this already?

I believe Simon (TiddlyDocs), Paul (TiddlySlidy), Mike (Trails) and Eric have done some work in this area, but I don't recall a particular plugin right now.


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