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I think what is fouling up your thinking is that you are considering this from the perspective of "what kind of sex does this person have." It has been my (albeit limited) experience that transgendered people do not have sex change operations in the name of their sex life, but, rather, so that their body better matches their gender.
A homosexual man is a man who is sexually attracted to males.
A transgendered man is a man whose gender identity is male, but biological gender is not.
So if you disassociate sexual attraction from gender: Pat could be attracted to males or females, but either way it is dependent on he or she, and not on his or her gender,
And if you disassociate gender identity from biological gender: Pat could identify as male or female, but either way it is dependent on which he or she feels is accurate, and not on his or her genitals,
Then your friend having a sex change operation only to continue having sex with men is not so much a flipflop or backstep as two separate decisions: (1) who he is, and (2) who he is attracted to.
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