The reasoning comes from, not only his fears that he isn't strong enough to defeat Vader after 10 years in hiding but the fact that facing Vader means Obi-Wan will have to face up to his greatest failure.
Losing Luke And Leia
Obi-Wan's biggest fear has to be the task he upheld for two decades, which was the protection of Luke and Leia. He spent his final years on Tatooine with the intention of watching over Luke, while the Obi-Wan Kenobi series detailed his efforts in rescuing Leia.
Darth Vader #26 finally addressed Anakin Skywalker's animosity towards sand -- by turning it into the embodiment of the Sith Lord's greatest fear.
He couldn't bring himself to kill Darth Vader, however, because he continues to associate him with the Anakin he trained as a boy. This is also the exact reason why Obi-Wan didn't kill Anakin on Mustafar despite the opportunity a decade earlier in Star Wars: Episode III - Revenge of the Sith.
He slays Sidious and returns to Obi-Wan, begging for atonement by execution, only to be met with true forgiveness instead. But just as this fantasy Obi-Wan refuses to strike his former friend down, Vader refuses to turn his back on the dark.
Obi-Wan knew it was only a matter of time. So, he made the difficult decision to use his learnings and become one with the force, rather than let Vader decapitate him.
In Star Wars Legends and Canon, Galen Marek (Starkiller) is the only Jedi (other than Obi-Wan Kenobi) to put a beat down on Darth Vader/Anakin Skywalker. Galen was secretly trained as a Sith Lord apprentice to Vader, but returned to the light side and the Jedi.
Luke Skywalker
However, once Luke fully embraced his power in Star Wars: Return of the Jedi, he proved that he was indeed stronger than Darth Vader and struck his father down.
Vader, the only power who overrules him is papa Palpatine. The reason why Vader obeyed tarkin was out of a sense of respect for him as a military leader, not as his superior.
Anakin admits to Obi-Wan that he has been arrogant and unappreciative of his training, and apologizes to his master. Obi-Wan assures Anakin that he is proud of him, telling him that he has become a "far greater Jedi than I could ever hope to be."
Yes he did. And the saddest thing is that there was nothing he could do about it. He was broken. The first case is shortly after ROTS when Vader was making his Sith lightsaber.
The short answer is yes, without a doubt, Vader regretted becoming a cybernetic monstrosity. First, there's the constant pain and discomfort from his suit. Worse, however, is the psychological pain. Vader destroyed everything he had ever known for a chance to save Padme.
#1 – Yoda. Yoda is widely considered to be the greatest Jedi of all time, and with good reason. He is a master of the Force, a skilled warrior, and has an unmatched wisdom that comes from centuries of experience. He is the embodiment of what it means to be a Jedi, and his legacy lives on long after his death.
McGregor explained that his character "can't reach out to any of the surviving Jedi for fear of giving himself away."
DARK SIDE FRIDAY - Did you know Palpatine feared Qui-Gon Jinn? Palpatine was immensely powerful and he could see the future which made him very confident about pretty much anyone who stood against him. So why Qui-Gon Jinn?
Biography. Legend had it that Yoda—a Jedi who became Grand Master—was trained by N'Kata Del Gormo.
1 Darth Sidious
There has been no Sith, as powerful, meticulous, nor as evil as the Emperor himself, Darth Sidious. As previously mentioned, Sidious trained in the Dark Side by Darth Plagueis before Sidious killed Plagueis in his sleep, making Sidious a Sith Master.
Aside from agility and telekinesis, Yoda could absorb and redirect Force attacks, like lightning. Because of his higher understanding, he would easily overcome Darth Vader in a fight, though that doesn't mean it wouldn't be a difficult battle.
Darth Vader : You have failed me for the last time, Admiral! Captain Piett? Captain Piett : Yes, my lord? Darth Vader : Make ready to land our troops beyond their energy field, and deploy the fleet, so that nothing gets off the system.
In the Star Wars Universe, it's hard to deny Darth Vader's greatest enemy was the Jedi Order. Sure, he had enemies such as Qi'ra, the Crimson Dawn and Doctor Aphra. But few came close to truly defeating him, other than Obi-Wan Kenobi and in time, his son, Luke Skywalker.
Why does Obi-Wan Kenobi age like that? Because he's not real, and is a fictional character played by different people. You see, Obi-Wan Kenobi is played by Alec Guinness in the original trilogy. Guinness was 62 when he filmed A New Hope, and he died in 2000.
For years, Vader hated Obi-Wan, having been struck down by his mentor and left for dead while also believing the Jedi had worked to turn his true love Padmé against him.
Darth Vader showed no emotion at all when he killed Obi-Wan Kenobi. If you watch the scene carefully, you will see Kenobi pausing. He was letting Vader kill him. Whether Vader knew this at the time, or discovered it later, is an open question.