Originally Posted by
Anymage
Death can be solved by a fifth level spell that the party can just pick up at ninth level. Hat of Disguise only costs about 500 gold in 5e, and under 2k in 3.5. And if we're looking at 3.5, any cheap magic item can be made with the "curse" that it switches the wearer's sex while held*. With the sort of magic that D&D worlds expect, transitioning should be achievable rather early into the character's career.
Which kinda goes back to what I said before. If you want to explore the day-to-day life of a person living in whatever sort of situation, you're going to want something aimed at that scope. When you're the person they call on to put down ancient dragons and eldrich abominations, little things like society's attitudes or the birth configuration of your body stopped being meaningful long ago.