I believe Nick is narrating this story not as it is happening but as it has already happened. When he told Gatsby that he was worth "the whole damn bunch," he was telling the story as he felt then. He reverts back to the present and says, "I've always been glad I said that."
Sometimes people look back on a situation they were previously in, and wonder why they were in it to begin with. Nick's feelings must have changed, not for the worse but maybe toward regret, since his experience with his chosen life in the East. Because he tells this story from experienced eyes, that may be why he does sound so detached and possibly "without judgment."
Nick was friends with Gatsby. . . at the time. Maturity may have set in and helped him realize the whole ordeal was not one to be looked up at. I liked Gatsby myself. He was a mysterious, interesting guy who, I felt, got misjudged or misrepresented by many characters in the book.
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