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I have been working on a project with something similar to that as the premise for a while now, though my Taliesin's not as genre-savvy and the timelines he goes between are all either medieval or of my own invention/amalgamation, not from modern retellings.
It would be cool if he bridged retellings as well, and that could make an excellent fic. What I'm writing is a bit different from that in flavor and I do hope to ultimately publish it.
Anyway, I see your vision and laud it.
Do you think there's potential if you can use Chief Bard Taliesin as The Fourth Wall/Meta Guy™ of Arthuriana?
As in, Taliesin - as a supernatural storyteller, arguably superior to the prophetic Merlin - being an almighty observer of ALL continuities of Arthuriana, able to know who is who, what happens in what version, and just being able to jump in and out of the different storylines whenever he wants.
One moment, Taliesin is hanging out in Caerleon-on-Usk, performing for Lucius Artorius Castus and then teleport on over to laugh at Monty Python!Arthur and co. getting owned by the killer rabbit.
In another scene, Taliesin talks about the different versions of the Grail Quest to Arthur and Peredur, giving comments about what he likes and doesn't like about each one, while expressing how he's annoyed with the French writers obsession with Lancelot and Tristan. Also, Taliesin gets to talk about all the different love interests of Lancelot and Gawain to French!Lancelot (who's in complete meltdown) and Welsh!Gwalchmai, who's like 😎
Taliesin predominantly hangs out with Merlin, his tutor Blaise and fellow aspiring bard, Sir Dinadan, inside Magic Treehouse!Morgan's Treehouse but every once in a while, Taliesin gets into an adventure and then brings along whatever character he needs, from Sir Segurant and Culhwch to BBC Merlin!Merlin and Fate!Artoria.