This is a limited partial answer addressing only Observation 2.
In this context, for Gita 9.32, the commentary of Sri Ramanuja (who lived in 11th-12th Century CE) might be relevant -
Sanskrit Commentary By Sri Ramanuja
।।9.32।।स्त्रियो वैश्याः शूद्राः च पापयोनयः अपि मां व्यपाश्रित्य परां गतिं यान्ति।
৷৷9.32৷৷striyō vaiśyāḥ śūdrāḥ ca pāpayōnayaḥ api māṅ vyapāśritya parāṅ gatiṅ yānti.
English Translation of Ramanuja's Sanskrit Commentary By Swami Adidevananda
9.32. Women, Vaisyas and Sudras, and even those who are of sinful birth, can attain the supreme state by taking refuge in Me...
By the usage of the word and (ca in Sanskrit) it becomes clear that women, vaishyas and sudras are differentiated from the "people of sinful birth". The verse is therefore not misogynistic.
PS: It cannot be said that the above is an example of a "modern progressive re-interpretation" of scripture, because Sri Ramanuja belonged to 11th -12th century.