There's also the author-insert character in Time Enough for Love having this "hmm, yes, I thought about going through a magic future sci-fi tech sex change, but ah, alas, it doesn't work at the genetic level!" reflection scene and his reaction to learning that even that "flaw" could be fixed is interest followed by dismissing it when the suggestion is genetically engineered and artificially grown clones, a mind copy, and killing the original body. Although the clone thing still happens and the female clones of the author-insert join his weird incestuous harem because this is a later Heinlein novel and they're all really fucking weird and horny like that. But overall that whole sequence is such a "no cis man sits contemplating becoming a woman and agonizing over every little flaw before rejecting it for the dumbest and most trivial of reasons" moment.