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If you mean automated-Crosswicking (commonly requested), there are more difficulties:
The entire wiki is article-based, which means all edits have to be done manually. Automatically moving edits to corresponding linked pages is a great idea, but without the move to database-style system it's not viable to implement.
Assuming there's a bot that can edit the pages like a normal user and is "done well" by addressing all the many drawbacks you mention (programmers charge a lot just to build something like that), most examples are unfortunately written with context of the page, it would be very challenging to tell a bot that by copying an example from a character's folder to a trope page they'd forget to mention who it applies to.
TroperWall / WikiMagic Cleanup
As things currently are, it is possible for a Work to link to/mention a Trope, without it having a corresponding entry on the Trope page, or vice versa. Meaning that some Tropes might have many works that link to them, but not have an equivalent example on the page itself.
This could either take the form of populating a page-specific to-do list, for tropers to edit the page, and provide an appropriate link back (with the linking line as context), having a separate page-section/menu that contains a list of Work/Tropes linking to the current Work/trope, or a commented-out automatically-generated section on the Trope page.
Besides Work/Trope links, this could also be useful for finding Works that might have sequel or prequel links missing, but are linked to by the Sequel/Prequel page.
The issues that I could see with this is that it might cause issues if Tropes are intended one-way links, such as for "See Also", or Super/Sub-Tropes.
It might also cause confusion if the Tropes are general/non-example pages, which should not have any Works linked to them, if users are prompted to add a new work to a page which should not contain examples in the usual locations (like Squick).
Such an automated system might also be prone to issues with abuse and spam. An edit war in a linking page over the relevance of a Trope, for example, might clog up the Trope's edit history with automated edits, or be used to spam the to-do list.
Functionally, if a menu is used to show the connecting pages, if there is a large amount of them, then it would be unusable due to the size of the menu. A similar issue would be present if there is a separate page, as a lot of links would make it a mass of text, or an enormous, barely-readable list.
From an implementation standpoint, there would also be issues where such a bot/system would need to be retroactively applied to all the Trope/Work pages at least, which is not a trivial amount of edits or processing, something that would put immense load on TV Trope's database and servers.
Additional work would also be needed to recognise links when made to sub-pages, such as a YMMV section of a work, or if a Trope's example works are large enough for it to be segmented into its own separate page, or else it would suggest duplicate works.
However, despite the drawbacks and implementation issues, if done well, it could be useful for ensuring that Trope and Work pages link completely with each other, as well as for locating erroneous links, or missing/broken ones.