I've always interpreted Obi-Wan's line to Satine about the fact that he would've left the Order if she asked him as an indication that, at the time when they were on the run together, he was still too young to understand the responsibility of being a Jedi, but every time I see it being used to argument that it must mean that Obi-Wan wasn't happy as a Jedi and craft the "fix-it" ending in which he leaves the Order I die inside a little
Obi-Wan literally said he “had [Satine] said the word [Obi-Wan] would have” and that phrase does not immediately ring “if asked [Obi-Wan] still would.”
It’s not even sly or tricky wording. I find it rather blatant. He would have, before, when they knew each other younger, but he’s not saying he still would. He is a Jedi master now; he has boundless bonds and connections and loyalty. I find it very hard to believe that he would leave now. Even if he didn’t have responsibilities fighting a war, he is very dedicated to the Order and his vow.
There are dozens of reasons why I don’t think it would have worked, and I think it would have worked even less at the time they were in the show or even after the war if things had gone better. I find it hard to believe that Obi-Wan leaning the Order for Satine/Mandalore would be a fix-it at all, but that is here nor there and probably deserves an entire different post.
Obi-Wan is happy in the Order; these people are his family and he doesn’t need that romantic bond/connection to be fulfilled and happy in his life. He loves Satine, sure, and he cares about her, but there are dozens of others he cares about just as much in and out of the Jedi Order and just because he doesn’t have a romantic lover, wife or whatever like Anakin, doesn’t mean he isn’t happy with the family and bonds he has. And the Order he has devoted his life too.
Obi-Wan was happy as a Jedi. He loved being a Jedi. It was who he was. It was his life. It was his choice. And he kept choosing it as long as he could. As long as it was an option - and even beyond that.