thanks for the analysis chief, so have you or haven't you?
p.s. even after surgery she is still, as you say, still a biological male.
When I was 19 I met a very interesting person who had lived as a pre-op trans for many years, though from what I understood, her "transformation" was not entirely voluntary. She was coerced by, of all people, her father.
When I met her, she self-identified as transgendered, even if the word hadn't been exactly coined (or at least in popular vocabulary) in 1979. She had breasts via implants (and had taken hormones for years), but was, in reality, a rather squat gentleman (with a staggeringly large penis) of about 40 years of age. She supported herself by making custom clothing for the drag and transgendered community in Boston.
She made me a custom shirt, which I paid for; we'd met through a mutual friend. As I recall, she still used a female first name, because that's how everyone knew her. We had sex once, which was odd and not terrible but not a top-50 (I've never been a fan of enormous penises, personally). Her breasts were interesting in a novelty kinda way; gotta say she wore men's clothes every time I met her, with bulky shirts and/or vests to disguise her breasts.
PS: once post-op I would define her as functionally female. However, her status as an MSM would depend largely on several factors:
1) Is she having sex with men or women? Many transgendered folks self-identify as oriented to the sex s/he's changed to. There are many more transgendered "lesbians" than you might suppose; for F2M I believe the ratio is even higher;
2) To what degree did she live a high-risk lifestyle while still biologically functioning as transgendered with a penis? MSM is a risk category, not a judgement (as I wrote above): did drugs, especially IV drugs and/or have high-risk sexual practices figure prominently in her life before final surgery? FWIW, many transgendered people live celibate lives prior to surgery, most others live quiet and otherwise entirely risk-free lifestyles;
3) To what degree is she psychologically anchored to her birth sex? Some transgendered people live to regret their change: admittedly a rarity, but it does occur.
One last thing: "queer" was defined as a non-judgemental term in the early 90s as shorthand for LGBT. If you're label-shopping, you'd do much worse.