How does Philo look at the inter-relations of Jews and Christians in the 1st to 4th Century AD? What do I need to read of Philo's work?
There is no evidence that Philo directly interacted with Christianity. However, he provides insight into the religious climate of Judaism/Greek thought in the Rome empire at the origins of Christianity. The Works of Philo | Logos Bible Software is a single, quite readable volume heavy on the allegorical interpretation.
I also like this "rearrangement" of the Philo text Amazon.com: Rediscovering Philo of Alexandria: A First Century Torah Commentator Volume I: Genesis: 9781506903491: Samuel, Michael Leo: Books Vote at Rediscovering Philo of Alexandria: A First Century Torah Commentator | Logos