This is mostly a hypothetical question, since I am leaning towards not transitioning.  But if I did...

I have a British birth certificate.  I am a now a Canadian citizen and resident.  The Brits have a process for changing the gender marker on their birth certificates.  For people who change their gender overseas (which would include me changing mine in Canada), you have to submit official government documents certifying your legal gender change.   But, as far as I can tell, the only official Canadian documents certifying one's gender change are amended provincial birth certificates, which obviously I don't and wouldn't have.

Has anyone else been in this position?  How did you deal with the documentation?

Not that it's a big deal.  I haven't had to use my birth certificate for anything in 60+ years.  Unless I have the misfortune to have to use a bathroom in North Carolina, I might not need it in future either, but you never know. 

I would think it would also include an amended Canadian passport and potentially your drivers license or other provincial ID.

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Over the last few months, I have completed most of my ID changes, including Birth Certificate, DL, Passport, SIN and medical. All were very straight forward. Being that I am in BC, I started with Vital Statistics BC and got the required forms, They have a help line that is very good. For Federal ids I also started with the government website. The name change and birth certificate process took about 5 to 6 weeks. The changes were important to me as I need to correct my passport and needed all the other IDs done first. I am also over 60.