2, 10, and 14 for Obi-Wan
2) Their emotional/moral weak spots
So I think it’s pretty obvious that Obi-wan’s emotional and moral weak spot is his attachment to those he loves. He raises Anakin (and makes himself believe in the Chosen One prophecy) because a dying Qui-gon asked him with his last breath. He ignores the mounting evidence that Anakin is beginning to lose his grip by the time the Crystal Crisis arc rolls around (Obi-wan won’t touch a blaster but has no problem with Anakin going Top Gun on a whole bunch of sentients? Yeah, someone is ignoring the problem/living out his darker desires through his student.) Obi-wan, I argue, should have killed Anakin on Mustafar, as it would have put a real crimp in Palpatine’s plans, but he was unable to due to the guilt. Obi-wan flies off to Mandalore with no backup to rescue Satine, an action that has far-reaching political ramifications in terms of the Jedi’s relationship with the Senate and Mandalore’s shaky domestic situation. And because of this, he backtracks so much that he allows Ahsoka to be tried and sentenced to execution, despite his protests. (Tell me Season 4 Obi-wan would have let that happen. Because he wouldn’t have.)
And he knows this is his weakness. It’s probably why he goes along with the Rako Hardeen plan, to prove to the Council (himself) that he is not attached. (And how badly did that backfire?) It’s why (this is conjecture, but I want this to have a reason), he never is in Dooku’s presence alone after AotC. Because he knows Dooku would play on Obi-wan’s attachments - because Dooku is an intelligent bastard who can see this from a parsec away and Obi-wan knows, deep in his heart, that there is a nonzero chance he would succumb because Dooku planted that seed of doubt how many years ago on Geonosis.
Obi-wan cares far too much and spends so much time trying to convince himself and others he doesn’t - that he’s as dispassionate and unattached as he projects, as the person he has cultivated is. And the tragedy of it is that desperation to live up to this standard lands him and others in hot water on more than one occasion.
It’s ironic, really, that Obi-wan, on the surface, plays the dispassionate Jedi Master but constantly battles with his attachments while Qui-gon, seemingly the maverick who cares for all living things, ends up being pretty distant to many of the beings in his life, once they get to know him. No wonder Obi-wan is somehow always trying to prove himself.
I would say Obi-wan’s largest fears have to do with failure. That he will have failed Anakin, the Council, the Jedi, the Republic, Satine, etc. It’s rare that we see Obi-wan actually scared, but that moment on Mortis when Anakin turns on him in the faux-Mustafar pit we do see him actually frightened - aghast that his actions have hurt someone he cares so deeply about. It’s fine if the consequences of Obi-wan’s actions boomerang back to himself, but it’s when those actions spell hurt for others - when all his good intentions, when all of his efforts fail and he is exposed as the Padawan who never quite could measure up to what Qui-gon wanted (in his mind). That, to my mind, is his overriding fear.
On a lighter note, I also think there has to be some of insect Obi-wan has an irrational phobia of, and one day he, Anakin and Ahsoka encounter it. It’s rare that Obi-wan acts so skittish around animals, but there’s something about the ten hairy legs, the hundreds of beady maroon eyes, the mandible clicking in that certain pattern that sets off Obi-wan’s fight or flight instinct (and it is decidedly flight). But Obi-wan being Obi-wan pretends that everything is fine, that he just finds the insects “rather distasteful” and tells Anakin “Why don’t you take care of it, seeing as you have such an affinity for bugs?” but both Anakin and Ahsoka see right through the lie and so during the night, they totally drop one or two into Obi-wan’s cot. Minutes later, they hear some very un-Jedi-like screams emanating from the tent and the two younger Jedi roll on the ground in laughter.
14) Ingrained habits/forces of habit
Well, we all know about the beard-stroking thing and the brushing dust off the shoulder thing (WHICH IS SO INHERITED FROM DOOKU I JUST CAN’T). I also have noticed (in TCW), that Obi-wan has a tendency to wrap his arms around his abdomen when he is hurt or feeling particularly vulnerable, which is an interesting piece of body language as it is a protective, distancing gesture and also a bit of self-soothing (which the brushing of invisible dust and adjusting of tunics also is). The self-soothing thing is so interesting to me, as it leads me to believe Obi-wan doesn’t open up to many people about his own issues (although he certainly tries to be a sounding board for everyone else, even Anakin) and that he, in a way, feels he has to comfort himself with that gesture. And, you know, it’s kind of sad but super-Obi-wan.