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If the Romans were so popular with the conquered, why did the Jews keep rebelling?

This is one of those situations where both parties were utterly baffled an unable to see the other person's point of view. The Romans found the Jews disturbing and confusing. Usually, a Province would quiet after the initial settling. Coliseums, indoor plumbing, and the relatively easy going Roman administration tended to win people over. The Jews, on the other hand, remained restive. There were all kinds of problems. The Romans found monotheism baffling, at it messed up their usual PR campaign. Jews did not want their god identified with Jupiter, baffling synchretism. They didn't even have statues.

Judaism presented other problems. Roman religion was a public thing. It was very much a State religion, but not just in the sense we mean today. Roman religion was practiced in public, for the Public Good. Romans had a deep suspicion of private religion, because not only was it incomprehensible, it was possibly treasonous. Plots against the government could be hatched. Deviant sex might be going on. It could be a cover for organized crime. They could be practicing witchcraft. These are all charges routinely laid by Romans against practitioners of secret religions (mystery cults in Greece, Cult of Bacchus in Italy, Judaism, and eventually Christianity). Basically, a religion involving private prayer and celebrations among small groups of friends creeped the Romans out.

The Jewish insistence on separate identity also stood in the way of assimilation. Jews were really resistant to things like intermarriage. The entire religion with it's discipline is perfect for keeping a people intact as a culture with or without a country. They resisted Roman attempts at assimilation with a vengeance. The tendency of the Imperial Romans to take teenage "hostages" from the royal family and raise them as guests in the Imperial family backfired with the Jews. Usually, after a few years of Roman education, opulence, and friendship with Patricians the young aristocrats would return and become a bridge between his people and the Romans. This backfired in Judea. People saw any Romanization as betrayal. This is unfortunate, since one of the best politicians of his era was the Herod in charge during Caligula's reign. He did a great deal to protect his people's integrity and autonomy and basically got spit on for it.

The Jews mostly saw Romans as invaders and oppressors. Attempts to assimilate them were scary because they undermined identity, their very Jewishness., the things that made them God's Chosen People. Kindness didn't work, since it increased the paranoia. They responded with hostility and occasional uprisings. They didn't want Zeus or Caligula or the God Augustus in the Temple. They wanted their daughters to marry nice Jewish boys. They wanted true freedom. I respect and understand this, trust me.

They expressed this through periodic Rebellion and the occasional massacre. One time there was a mass uprising where the Jewish colony in Cyrene rose without warning and simply slaughtered a third of their gentile neighbors in their sleep.

This kind of Terrorism did nothing to dispel the Roman fear of private religion and reinforced the image of Jews as lunatics. Thus, it was easy to brand Christians as cannibals later. The Romans simply had no clue what was wrong with the Jews. The Jews couldn't understand why the Roman's didn't let them go. Basically, the cultures and world views were incompatible.