I liked the Montage also. One suggestion.

I'd include some shots of Anakin from the Arena fight at the beginning of the montage. So that you can show him with his Padawan haircut. Then I would use the shots of him flying the fighter at the end of it so that you can see his Sexy Jedi Knight haircut and really indicate that it has been a while. Then you can end the montage with them crash landing on the ship and him getting out. Calmly and that should seque nicely into the realization that he and obi are now equals.