Men entering into any field where women are traditionally welcome are seen with suspicion by society.
I'm sorry, but that to me sounds like an attempt at spinning a reality to turn it on its head. So it's not that men are seen with suspicion when being near children, it's because it's actually because it's a woman's job and it just proves how women are considered inferior because men who get these jobs are considered weird for "lowering" themselves to women's level. Isn't that what you meant? Am I wrong in my understanding of what you said? But this way of spinning things can't explain why some airlines have rules that says that adult men, and only men, cannot sit next to unaccompanied minors. This is just one of many cases like this.
I feel like you want to do good, but you're stuck between recognizing these situations, and an dogmatic academia that claims that men cannot be discriminated against as men because they are "privileged" and have the power, so it would make no sense for men to create a society that discriminates against men. So the only way to reconcile these two positions is to someone twist and bend the facts so that they fit in the ideological point of view of the "academia" you are part of: it's not men, it's actually women who are discriminated against and it's just that these men are like "collateral damage" by opting for traditionally feminine jobs or the like.
All men who do any job other than stay home or those traditionally allocated to women are seen as being within their gender role. So long as a man is not actively engaging in sex with other men; however, he will still have a higher position than a 'traditional' woman.
All women who stay at home or who do jobs not traditionally allocated to men are seen as being within their gender role... Society considers gender a binary system, all jobs will either be traditionally associated to one gender or the other. Saying that one person will be seen as within their gender role if they don't have jobs that are traditionally associated with the other gender is trivial. It's like saying "any real number which isn't negative is positive" (okay, except the 0, which is both).
I highly disagree with the second sentence. Do you really believe that an homeless man is seen as having an higher position than a housewife or a female high school teacher? That is what you are implying, and I'm sorry, but it makes no sense and clashes with reality.
To answer your final point- welcome to the Procrustean Society. Men are put into greater pressure to conform to the traditional social structures than women are because women are not men. Women are less than men. If a man fails, then he is a failure as a MAN while if a woman fails, she's just a weak woman. So, yes, if a man fails, he is likely to end up on the streets because he is taught by tradition and a male privileged society that he is a failure as a man and thus must be cast off. Men are taught to break under adversity while women are taught to adapt. Men who adapt, though, are viewed as not-men and thus lose their privileged status.
I disagree with that interpretation. I think it's another case of ideological academia trying to fit a round peg in a square hole. You can easily see it another way: women have inherent worth in society, men don't. Men have to continually prove themselves in order to be valued. This is usually done through work or demonstrations of abilities. Hence why men in trouble or distress, for example men who cry, are generally not met with compassion but with irritation, even anger. "Be a man", they will be told, or "take it like a man". Under these reactions is the implicit affirmation that they have to deal with their problems by themselves, because they don't DESERVE assistance, they're not worth it.
BTW, last time I described this hypothesis, a transwoman on the site I posted it on actually said that it made a lot of sense from her perspective. That it "...makes a lot of sense in why trans women are more punished than trans men, for being trans." (her words, verbatim).
This is a very complex discussion, and I feel that while you and I are making the same points, we're not using the same vocabulary. I do have trouble with the term 'privilege' as I prefer 'status', but in academia the term is 'privilege'.
The vocabulary isn't innocent or trivial. I think the obsession about using the word "privilege" is clearly part of some kind of Oppression Olympics from the academia you talk about, it's about clearly identifying an "oppressed" and an "oppressor". It is, quite frankly, insulting. As an unhappy male like so many other, the use of the word "privileged" to describe my life is not only denying me the right to define my own life experience, but actually claiming the right to define it for me, and defining it in a way that says that no matter how bad I may feel, I actually deserve less than I have, that I deserve to be brought even lower and that I should apologize for, basically, existing, as my existence as a male is seen as taking opportunities away from women.
There's a reason why the rhetoric of the "academia" you speak of stays confined to it and to certain activist circles.