| This is also a solved problem (largely) around trans issues specifically. I suggest reading http://www.glaad.org/reference/transgender for more context. In particular, you should refer to Chelsea as she would want -- with her current name and her expressed gender pronoun preference (e.g., use 'her' where you use 'his' above). Also, "gender association" is not a common formulation. In terms of capturing the nuance of acts prior to public transitioning, the above link has some suggestions: Avoid pronoun confusion when examining the stories and backgrounds of transgender people prior to their transition.
Ideally a story will not use pronouns associated with a person's birth sex when referring to the person's life prior to transition. Try to write transgender people's stories from the present day, instead of narrating them from some point in the past, thus avoiding confusion and potentially disrespectful use of incorrect pronouns.
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I'm not really sure how to square that with myself, but I think I lean towards preserving the data integrity of the public record. If someone referred to themselves in a specific way and identified themselves a specific way in the past, I think that's how they should be referred to when discussing that point in time.