Being conversant with Greek philosophy and the Latin language would have made him suspect in the eyes of his people, but his decision to cast himself as a Pharisee made him acceptable. It was good cover for a questing, restless mind.
Inheriting a Roman citizenship from his father and grandfather gave him a passport to the Pax Romana, which was an advantage afforded few Jews. Witness what happened when a provincial Roman governor put him in jail without a hearing, and the panic that ensued when the governor realized his mistake. You don't mess with a Roman citizen. Heads roll for less than that.
Had you met Paul outside of the ritual known as "The Lord's Supper", your exquisite koine Greek would have permitted you to argue philosophy and politics over red wine. He would have loved the intellectual stimulation. (The Romans engaged in the kind of Greek-versus-Italian wine debate that mimics the French-versus-California wine debates of the Seventies.) Unfortunately, had you opened your mouth during religious services, he would have said, "Dear lady, be silent."
He had this blind spot with women. Marriage might have cured him of that.
It was possible that Paul’s ‘Blind Spot” was thoroughly appropriate in Corinth, where the “Church ladies” were really making a mess of things! (Some still do!)LOL. As a woman who has been in ministry for over thirty years, I would have been with Paul, telling these viragoes to “put a plug in it”.
However, in other communities, Paul was very complimentary of various ladies (Lydia, Priscilla, et al) who had churches in their homes, or who were paragons of Christian Hospitality.
I read the Book of Acts every night, and greatly enjoyed your post! I just finished reading the very section you described!
Anthony Hopkins did a decent job playing Paul in the miniseries “Peter and Paul”.