Always keep fighting.

Imagine it:

Yoda is the Grandmaster of the Jedi Order. He has the ability to make lasting changes to the order in a way that young Padawan or newly knighted Obi-Wan alone couldn't. He's also had ~25 years alone in a swamp without even the passing human contact Obi-Wan got on Tatooine to reflect on all the things that went wrong, and stuck around as a Force Ghost at least until TLJ.

Not that I imagine TLJ happening in this AU - to kick it off I imagine Luke not managing to make it off the second Death Star after Anakin dies, and Anakin and Leia's anguish in the Force managing to hurl the watching Force ghosts into the pasts, where they can keep Luke's death from ever happening.

And so you have Yoda and Obi-Wan being thrown back to, say, 52 BBY. Obi-Wan, now only five years old, wakes his crechemate's up with a "vision", and for decades afterwards the younglings swear that on certain nights you can year an echo of absolute and complete anguish in the Force.

But the end result is the same: 5 year old Obi-Want has his memories of the next 52 years alive and 4 additional years of being a Force ghost. The transition is somewhat less abrupt for Yoda, who is 800+ at this time.

Unlike Re-Entry, the only one Yoda and Obi-Wan tell (at least at first) that they've traveled through time is Mace - and only then because Obi-Wan is very obviously not a normal 5 year old anymore. (And even then it's more of an accident Mace finds out. Instead Yoda just sort of pushes Mace at Obi-Wan "to help him get a handle on his visions and train him in the ways of the Force", and in the end Mace finally puts two and two together after sort of assuming he's just going crazy or being punked.)

Actually, confused!babysitter Mace is half the drive for this plot bunny. He's so confused and Yoda is being even more of a troll than usual, and he's not prepared at all to deal with such a small child, but honestly half the time it feels like Obi-Wan is the one taking care of him, and just so much confusion.

Together, between Yoda being the Grandmaster and Obi-Wan's weaponized cuteness as a youngling, they are able to prevent some things that contribute to the fall of the Republic. (Galidraan et al).

Obi-Wan is taken as Mace's Padawan fairly young, and no one really considers it too be too odd how good he is so young given that Mace was his Master and Yoda's been his mentor since the creche, but he's definitely considered to be an odd child. As one might expect of a ~60 year old being suddenly stuffed into his 5 year old body. When it eventually comes out that he's a time traveler, it answers a lot things people didn't realize they were questioning.

But mostly confused!babysitter Mace, troll!Yoda, and baby!Obi-Wan.

As always, feel free to adopt the bunny. Just link if you end up doing anything with it.

Obi-Wan: (notices Mace) oh, Master, please join us.

Mace: ... (Sits down)

Obi-Wan: (Sighs like an old man) I must say I'm glad not to be on the council at the moment. Have you read my proposal on Hutt investments portfolios? I know you're busy with Xanatos' nonsense, but if we move soon we could prevent Jabba from gaining ground in thirty years.

Mace: you should be learning how to mix colours with paint, not sending me paperwork in the middle of the night, Master Kenobi.

Obi-Wan: (gestures to neat paint pallet with colours mixed) I already know how to do that.

Yoda: doubt that I do. Knowing is not understanding.

Obi-Wan: that doesn't even mean anything. You can't tease me just because I'm small now.

Yoda: size matters not. Tease you I always will.

Obi-Wan: well that's true (eye roll)

Mace: I have enough paperwork Kenobi. Stop sending me paperwork.

Obi-Wan: well I would send it to another Master, but you're the only one that knows of my predicament and you won't let me use your name, and Master Yoda has always been awful with written proposals, no one would believe it.

Yoda (has brought out the paints Obi-Wan had with him and has started mixing colours)

Mace: Master you can't just mix paint on the tile!

Yoda: fear the mess it will make, hmm?

Obi-Wan: you're impossible. (Starts doing it as well) I never enjoyed making a mess, even at this age.

Yoda: fear of the future that is.

Obi-Wan: here he goes.

Yoda: to live in the moment, without fear of the mess of the future, that is the way of a Jedi.

Mace: (watches the two of them paint pictures on the ground. It's a complete mess)

Obi-Wan: I don't fear the future.

Yoda: hah!

Obi-Wan: I'm stressed! Stressed isn't the same thing as fear.

Yoda: come from fear stress does. Anxiety. Make a cloud you should.

Obi-Wan: (examines his tile of art work, adds a cloud)

Yoda: stress Master Mace has trouble with too. (Pointedly looking at Mace who is just watching the mess unfold)

Mace: (sighs, takes the hint, sits on the floor and dips his finger in the purple Obi-Wan mixed) I have many things to do.

Yoda: but right now you are painting.

Mace: I can't tell if you're both being serious or messing with me.

Obi-Wan: it can be both, Master. (Makes a face) I'm going to have blue hands for a week.

Mace: have you always been anxious, Master Kenobi? You always seem very confident and composed. It was eerie when we first met, seeing a child so poised.

Obi-Wan: yes, well I don't want anyone to know I'm anxious. Too many people rely on me.

Yoda: like someone else that is.

Mace: well... Right now you're at an age you don't need to be so independent.

Obi-Wan: I'm older than you are, Master. My crude matter doesn't reflect who I am inside. I can't just turn off my worries. It was easier in the end. In the desert... But it's hard to grasp now. I found my balance and peace, but in the here and now I find myself at odds with my knowledge. Every stray thought and memory of something that could be changed for the better.

Mace: changing the future is dangerous.

Obi-Wan: not changing it is more dangerous.

Mace: if you become obsessed you risk losing yourself. You need an anchor.

Obi-Wan: I know. (Focuses back on his painting) The future is always in motion. I am not changing anything. I am simply existing in the now. The ripples for good or ill can rarely be controlled or focused. However is it not my duty to follow where the Force has led me and do good?

Mace: ... (I feel very young suddenly)

Yoda: talk too much you do, Master Kenobi.

Obi-Wan: well it's been awhile since anyone has been kind enough to listen, Master Yoda. Force knows you don't have the attention for it.

Yoda: accuse me of senility do you? Focused I am on the present (gestures at his paint mess). Rambling on the old days you are.

Obi-Wan: who is the more senile? The old man or the old man that tries to talk to him?

Mace: (looking at the five year old who just said that. He has a splotch of blue paint on his cheek) no more proposals in the middle of the night, Kenobi. You'll get an ulcer at six.

Obi-Wan: (prim and proper) and when exactly did you get your first stress ulcer Master Windu?

Yoda: (laughs) twenty-two he was.

Sifo-Dyas is a particularly intriguing character to look at through this lens. He is a rare thing in the saga: a Jedi who is portrayed outright as living with a disability (and/or mental illness).

This is not a case of a hero whose hand is cut off and then it’s never mentioned again because sci-fi tech has effectively "solved" it with a fantasy-perfect accessibility device. Neither is he relegated to tokenism or moved to the sidelines to play quest giver. Uncommonly, Sifo-Dyas's symptoms are realistic and have severe consequences, while he’s also simultaneously depicted as an active Jedi Master with tremendous power and responsibilities, both in universe and in his narrative role to deliver the plot setup for the entire prequels. 

First off, can we even call the depiction of his visions disability-coded? Without applying real world diagnoses to fictional characters, I think we can summarize that he:

has severe neurological events which routinely place him in physical danger (he collapses midfight in the middle of a battlefield, his post-Knighting travel with Lene is contextualized - by Lene herself I believe - as care)

has devastating chronic symptoms (Lene's account of often finding him curled up in a ball in his quarters weeping), that have a meaningful impact on both his relationships and the work that he wants to do. 

the threat of being not believed, and even institutionalized, are ever-present specters looming in his story. While this is in the context of fictional psychic abilities, it’s hard to read scenes, where, for example, Lene Kostana worries about a teen Sifo-Dyas being taken away from her training and locked away in the Citadel, without a chilling real-world echo with how some disabilities and mental illnesses are, or have historically been, treated.  

At the same time, we could argue that Sifo-Dyas is one of the characters who exhibits the most agency in the (pre)prequels. His narrative role is as the guy who peers behind the curtain, who sees the plot and tries to change it. From trying to save Protobranch when he was sixteen, to the attempt to flood the Order with Jedi in his Seeker days, to the inevitable clone army, Sifo-Dyas is personally, actively, deliberately engaging with the plot. While his visions have consequences and other characters are visibly aware of their impact on his life, he still progresses from Knight to Master. He seems to have sat on the Jedi High Council for a number of years and is going on active missions well after that. In the Living Force novel, Mace Windu implies that the Council’s entire ability to see the future has been compromised by Sifo-Dyas’s death. 

I got to thinking about this because I made myself sad about the cover story of Sifo-Dyas's "death on Felucia." The version of events the Council had for years before they uncovered the shuttle/Dooku connection near the end of the Clone wars.

On overview, it's such a bitterly believable story. A guy who publicly struggled his whole life with a debilitating, unpredictable power becomes increasingly destabilized, loses his job as a Seeker, and gets eventually kicked off or "resigns" from the Council after a big disagreement with them. Shortly afterward, he loses control of a tribal conflict on a mission and is killed. Off-screen funeral. Lightsaber doesn't make it back to the Temple. How much did assumptions of spiraling mental instability after a lifetime of living with with a debilitating condition impact how willing people were to believe a version of what happened to him?

Of course, the real reason Sifo-Dyas’s death isn’t properly investigated at the time is not because it’s meant to be a parallel to real life stories where police treat cases of missing people with mental health differently, but because there’s a massive coverup by the Sith, notably the Sith running the very Senate that sent Sifo-Dyas to his actual doomed mission instead of Felucia. (I’m very dubious of the Jedi Order treating Sifo-Dyas badly specifically because of his visions - the implications come only from Dooku who has AMPLE reasons to be an unreliable narrator about them, but that’s a whole different post.) 

I have serious doubts about most of this being intentional, considered representation. So much of Star Wars theorycraft boils down to piecing inconsistencies into order, and Sifo-Dyas, the bastard child of a typo and half-scrapped first drafts, is a masterpiece of the kind of storytelling that creates these cracks. The contradictions in the character – chronically debilitated by his visions but a powerful, actionable high council member – could very well be not thoughtfully-considered representation, but an oversight that actually turned out in a really interesting way.