You need to use your imagination. For instance, you said your friend was fine with these questions right? So let's do a little thought experiment:
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Hey, my friend James who happens to be African-American, why do you love watermelon so much? Is it because of the flavor? The texture? Is watermelon something that all people like you like?
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In that case James won't punch you in the face ... probably (depending on how good of a friend he is). Especially if you leave off that last question. But then try asking the same thing to a public forum:
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Hey African-American Project 1999 players: why do you love watermelon so much? Is it because of the flavor? The texture? Is watermelon something that all people like you like?
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Hopefully that made you wince.
Now obviously transgender people have neither stereotypes about watermelon nor about raiding in EQ. But they do have stereotypes of being "the other", or being different, and of being defined by their gender identity.
Your questions reveal a ton about your own biases and how you see transgender people. For instance, you clearly see transgender people as being so different from you that their gender identity could (at least potentially) determine every aspect of how they play EQ. If that wasn't true, why would you ask the questions you did?
But if I asked you "do you play a cleric (or raid, or whatever) because you're a straight cis-gender male?" you'd probably say that's a stupid question.