I'd start by asking is this a reciprocal social contract? With equal expectations?
Because I think you're positing some people as carers and some as rather infantilised and helpless recipients of care.
Is it going to be men without trans identities doing this caring work?
Is this contract and set of expectations equal, and how healthy is it if not?
Isn't this #bekind? How sensitized have women become to this phrase and what's the reasons and experiences that sensitized them? Was that phrase used in a manipulative way to gain reluctant consent and labour? To lower boundaries and permit what they otherwise wouldn't have done?
I don't think many here are talking about teenaged vulnerable girls with Autism, we're talking about the kind of men you can find on many threads here. Two in the past 24 hours for example, one of whom discussed their imagined response of flashing, a sexual assault, on non consenting women in toilets to punish them for non compliance, and the other of whom is hinting heavily about how women wanting privacy, dignity, rights, tolerance, are being discussed on a voice chat with their messages in a rather sinister way, with absolute derision. Women have been raped, assaulted, beaten up, excluded, in the name of well intentioned but compulsory indulgence of these men - and those women were sent to indulge and get the consequences , those setting the policies weren't taking those risks or having those experiences themselves.
The last elephant in the room in all this is that for many adult men transitioners, this is largely a sexual experience, and the use of women as resources and props within that experience is crucial. Hence the absolute rage when those props won't co operate, and the desire to gain the non consenting ones. As a psychologist you'll be well aware of the criminal psychology basics of how the distress or anger or emotions and reactions of a victim increase excitement, it's 101 armchair stuff these days. Two minutes on Terfisaslur.com shows the degree of pathology and disturbance involved for not some, not a few, many.
How healthy is it, honestly, to say to a woman when confronted with a man who has already declared what he thinks of her, her boundaries, her equality and her purpose in this experience of his by walking into a single sex space, that her first thought should be sympathy and understanding for him? Why is he entitled to that energy and head space from her? Why should she lower her guard and instincts, and extend this trust and caring role?
It's lovely for him, yes. What does it give her? Other than how lovely it is to be nice? At least until he hurts you.