I'm not sure if this helps or is relevant. I'm an academic with quite a long track record that I need to preserve, so changing my name became quite a topic of discussion among my medical team who know me professionally as well. In the end I decided to feminize my first name so that the initial remains the same. My second name I changed to Cindy and I kept my family name. So, I've ended up with the same initial, so my track record is easy to follow, my feminized first name is very easy for people to use as it doesn't need a great grasp of memory, and my middle name is what my friends use. I'm very comfortable with my first name as well so I don't feel in any way slighted by people using it. It is also interesting that people hear others use Cindy in reference to me and I hear people say, Oh I thought her name was now XXXX, and then I hear the glee in a persons voice as they say, 'Her friends use Cindy, XXXX is her professional name'. Then someone else calls me Cindy - so they can be my friend
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I have changed my name on many documents but my understanding is that both my original and new name are legal on signed documents, such as mortgage and such as it was then, my legal name. My Will etc under my male name is still a legal document which would be honoured, so I'm told. But these things seem to vary a lot from place to place.
Of course if you have debts they don't care what your name is, they will still pursue you
Cindy