Do the Gedolim show sufficient sympathy for women's concerns?

Toby Katz asks the question on Cross-Currents and answers that of-course they do; you don't need to be a woman to understand women's concerns. She then brings a story about Reb Aryeh Levene showing empathy to a woman to illustrate -- more on this in a moment.
House of Hock offers a good response, which comes down to four points:

• Showing sympathy and human kindness to someone on an individual level isn't the same thing as understanding their concerns on a communal level
• Most of these rabbis live in mostly male environments -- thus their real experience of women's concerns is limited. Even if they understand the needs of the women in their immediate community, they probably won't understand the needs of modern orthodox, or more moderate charedi women etc.
• Even if you do 'understand' someone, this doesn't mean you're going to be their best advocate, or even that you're going to stand up for their needs at all. This to me is the most imortant point.
• The proof is in the pudding: they're still coming out with all kinds of rulings which women find objectionable and, I would add, there are too many women out there who feel that their needs and concerns are not being addressed and indeed, have no address.

I would also add that Toby makes a hillarious choice of story with which to illustrate that male rabbis can understand women. It concerns the Tzaddik in our Time (my distant mishpoche, incidentally) going to visit widows of great rabbis, because he understood how lost they would feel without the husband who defined their lives:

With her famous husband gone, such a widow becomes a non-entity, bereft of identity and of respect and acknowledgement. It seems to her that she is nobody, and that her beloved husband, too, has been forgotten. But when his former colleagues and students come to visit, she comes alive again. She serves them cake and tea as she did in the old days, and they fill her ears and heart with reminiscences of the great man around whom her life once revolved.

Now, I'm not disagreeing with the psychology here. But is a story about a rabbi understanding a woman who feels she's nothing without her husband and that she is just aching to serve cake and tea to young men again really the best way to reassure modern women today that rabbis are aware of and sympathize with their concerns???

UPDATE: Modern Orthodox Woman adds her thoughts.