I just rewatched this, the one that went from the training scene to the elevator and honestly unless you’re looking for the differences they aren’t that obvious between Anakin. As for Obi-Wan, I think it works, the hair/beard difference because of what is going on. Obi-Wan’s hair changes and gets all ruffled because of the fight so it’s all messed up and out of place by the end of the training scene. So we begin the elevator scene it’s all sleek and nice, plus!, his beard is trimmed BECAUSE he is going to meet a senator (yes, one he’s met before, but still) be her protector.

So, yeah, the fact that Obi basically got a fresh trim and cut/style to his hair makes perfect sense as to the change in his bear/hair. And, again, unless you’re looking for it, it’s just not that obvious with Anakin. So, I think it really does work. Also, that’s with the scenes back-to-back. Having the Padme scene with the chancellor between the two would make it work even better and those changes even less noticeable.

A de-aging deepfake on Obi still would not be a bad idea, though.