I think a lot of it is that he misconstrued how Anakin learns, actually. I mean, he is attached, for sure, but I think the bulk of that (particularly that which was inappropriate for Jedi, both in intensity and type) happened after Anakin was knighted.
Because Anakin was starting from behind in so many ways, and yet a little prodigy, there were no good bench marks for Anakin’s progress. I feel like Obi-Wan decided that what was most important was maturity, which Anakin distinctly lacks in AotC. But the Council and I think most other Jedi Masters were using the benchmark they had – abilities. Most Jedi can’t achieve the abilities Anakin has without maturity and deep spiritual contact with the Force. So Obi-Wan is frustrated by the fact that he can plainly see that just because Anakin is a gifted swordsman, mechanic, and basically you name it, that doesn’t mean he’s mature enough yet or emotionally equipped for solo missions. The Council is like “Obi-Wan, cut the apron strings, I’ve seen what that kid can do.”
And as usual they are both simultaneously wrong and right. Anakin has the abilities without the proper mental and emotional states, but he does far far better when you trust him and give him a chance. When it’s down to just him to be responsible (barring horrible murderdreams and a certain Senator), he comes through every time. TCW actually shows him holding himself together better than I would have ever predicted and I’m ridiculously soft on him.
Ahsoka is healthy for Anakin because not only is she a great person and a good friend for him, she’s also someone he can learn responsibility through and become a better Jedi for. And for a time, he gets to live the dream, because I think the Council consciously told Obi-Wan stick around as training wheelers for Jedi Masterhood. They think that they’ve put Anakin in the middle, learning what he needs to from Obi-Wan while teaching to Ahsoka (and in turn learning), but Anakin actually got a Jedi family out of it. Everyone is happy and everyone thinks they’ve got the other side duped.