But in most respects I don't think like an ancient Jew and that might explain why I am puzzled that Rome and Dema Roma were thought of as being whores by ancient Jews.
The ancient Jews had horrible attitudes towards women. The portrayal of the misdeeds of a nationality as the activities of an unchaste woman is actually a recurring theme in Judaism. You're familiar with the sexual escapades of Oholah and Oholibah (Samaria and Israel respectively) in Ezekiel?
Denigrating foreign deities and their visual representations was also common in Judaism and that crosses over into the Bible as well. To me, it's not surprising at all that the two would come together, because it would not be the only example of its type.
My purpose in posting the image of the coin was only to show that the motifs are echoed in Revelation. She's clearly seated upon the seven hills of Rome (cf. Rev 17:9) with her feet at the edge of the Tiber (cf. 17:15) just as she's described
There is nothing in that depiction to suggest unchastity and I am puzzled that you seem to be looking for clues for it. The viewpoints of the Romans (Who minted the coin) and the Jews (Who hated Rome) are diametrically opposed and you're not going to find evidence of the Jewish viewpoint on a Roman coin.