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Let's say that Obi-Wan goes back to a point in TPM, just after Qui-Gon’s about to say then he’ll train he boy, Obi-Wan tells Anakin to leave so the grown-ups can talk and after much convincing about where he's from explains that the Council’s right and the boy shouldn’t be trained. Then, Qui-Gon says that Obi-Wan being sent back in time must be because Anakin IS the Chosen One, so he still plans to train Anakin. Obviously, he’d prefer to have the Council’s backing with this, and clearly he can train Anakin since Obi-Wan’s already a Master in mental years. Would you rather supervise me training him or let me go rogue? So the Council reluctantly agrees.
Then Qui-Gon goes a step further and argues maybe it’s the Will of the Force that Obi-Wan be the one to train Anakin. Obi-Wan is dead set against this, but Yoda asks if it fear that is stopping him? Is it losing Anakin again? Attachment? Blah Blah Blah. Ironically, Obi-Wan ends up training Anakin again, but Qui-Gon helps so much it basically mirrors Ahsoka’s training with Obi-Wan as primary master and Qui-Gon the hovering Jedi Master. (The Council also backs this move of making Obi-Wan train Anakin again, because if the boy must be trained, rather have Obi-Wan whose more likely to listen to them than Qui-Gon who just won’t.)
This doesn't necessarily make things better, because Obi-Wan is being even stricter this time around to ensure Anakin doesn't fall in the trap of "attachement," and while it’s nice to say Qui-Gon could do a better job, however maverick he is, he’s still a Jedi of the old Order who has the Council’s respect, even if they’re frustrated with him. He’ll fail Anakin in many innumerable different ways, because the Order’s methods remain toxic. So they isolate him and condemn attachment more than ever, BUT as Qui-Gon isn’t afraid of Anakin like everyone else (even Obi-Wan), he doesn’t “hold him back.” Therefore, Anakin delves into his powers more than ever before. He doesn’t hold back like he used to and this means all kinds of problems as he starts getting too much feedback. Eventually, Qui-Gon and Obi-Wan have to take him off to a planet by himself until he gets the Force under semi-control. The problem with this is the Council is even worse to Anakin now that they have that much more reason to fear him, and Anakin can sense it too. So, he’s even more isolated and angry then before, and also quite a bit more capable in his abilities.
Meanwhile, the Council tries to figure out what to do about Palpatine. They either go in and take him down, in which case the Order comes under extreme attack because how can they justify this murder? He’s a Sith? Is that illegal? How do you know? Where’s your proof? Time Travel? What’s more likely though, is they try to find dirt on Palpatine, and fail…because he plays the game so well. So they try to arrange “accidents,” but Palpatine can see them coming so they’re REALLY on edge.
Obi-Wan spends most of his time freaking out, because Palpatine’s impossible to handle, Dooku seems to have fallen anyway, or at least founded the CIS because he’s a “political idealist.” What the kriff??? BUT if that weren’t bad enough, Anakin seems to be more volatile and insecure arrogant than he even was before. Where are they going wrong? Ultimately, Anakin is probably going to snap from the pressure. Then what? Provided nothing goes wrong until the Clone Wars, Anakin is in the army now and easily getting close to the Chancellor. What should Obi-Wan even do?
What’s honestly more likely though is that won't even have to become a concern for Obi-Wan, because Anakin snapping and running off will occur WAY before then, because it’s just TOO MUCH the way the Council and everyone treats him, and Dooku (who would have told Palpatine about Anakin), stays longer than he did the first time around, (since Qui-Gon is alive), just to manipulate him on his master’s orders. Perhaps he even brings him to Palpatine? Or, BETTER YET, Anakin leaves with him to join the CIS, and help found it too, because maybe then sh*t would get done. (The slaves!) Canonically, I believe, Dooku never had faith in Anakin as the Chosen One, and thought the Council put undo pressure on him, and the Council ought to just take matters of the galaxy into their own hands. If they did that they wouldn’t need a Chosen One. He said “They follow the Will of the Senate, not the Will of the Force.” Anakin can get behind that; he agrees with that, and since Obi-Wan never thought that a Dooku who hasn’t fallen, (and why would he fall if Qui-Gon didn’t die?) would be such a threat, doesn’t see this coming. After all, the main problem was Vader: The Dark!Chosen One. But then off Dooku goes with Anakin. What the Kriff?!!!
I dunno, I’m just brainstorming here, but I think Old!Obi-Wan’s presence will just make Anakin worse off than the first time around, and more likely to fall. Worse still, with no “attachment” in his life, worse than even the first time around, whose going to get through to him to save him? Ultimately, I think Obi-Wan would get desperate enough to basically plead with Anakin and it all comes out that he’s from the future, and Anakin can sense that this is true, eventually, and this leads to forgiveness from Anakin, but he’s still going to be upset with the Jedi, and isn’t likely to want to return to the Order, because clearly they weren’t so great the first time around either. I won’t fall, Obi-Wan, he’ll say, but I’m not going back.
Poor Obi-Wan. Now, he just doesn’t know what to do. He meant to spare the galaxy of Vader, and maybe he has, but how does Anakin becoming a Separatist make matters better? It’s still dangerous! He’s left the Order and forming attachments left, right, and centre, and he’s bound to Fall, even if he doesn’t mean too, even if it happens in a different way. Now what?
Poor, poor Obi-Wan. He tried to make it better, maybe he’s made it worse. Now, he just doesn’t know what to do.
(Honestly, if you really want to fix the timeline, send Padme back. It’ll go much better.)