Most Hebrew scholars believe the birth of Jesus took place in the fall, not at the winter solstice. Why? Because of the timing of John the Baptist’s birth. His father was serving according to the schedule of a specific division of priesthood, and the records are known of when this division served. And we know that John the Baptist was six months older than Jesus.
We also know that all the cities round about Jerusalem were packed (of which Bethlehem was one) because Joseph and Mary could not find room in an inn. It was during the Feast of Tabernacles, when all the males in Israel were commanded to appear in Jerusalem during the feast.
The shepherds in Israel did not pasture flocks in the dead of winter — but during the high holy feast days, of which Tabernacles was one, they kept flocks around Jerusalem for sacrifices. Jesus, or Yeshua, means “salvation,” and His prophetic name, Immanuel, means in Hebrew “God with us,” (Isa 7:14, Mat 1:23). Tabernacles is the feast that celebrates God with us – God tabernacled (dwelt) with Israel in the wilderness. On the eighth day of the feast, the seventh special high sabbath of the biblical year, Yeshua was circumcised, or entered into the covenant of His forefathers.
Even a cursory reading of the nativity history in Matthew, and Luke, reveals glaring differences. The key to understanding the narrative, is to realize that the events which took place with the wise men, occurred up to two years after the birth of Jesus, for when Herod slaughtered the baby boys, he killed them all from two years old and younger (Mat 2:16). Another clue, is that the wise men visited Jesus in the house where he was staying (Mat 2:11) — he was not in a stable, not in a manger. So what were Mary and Joseph doing back in Bethlehem two years later? Well, they went up for the feast every year, just as they were commanded by Torah.
Now as to Simeon, he was waiting for the appearing of the Messiah. He knew when it would be, because the prophet Daniel received a prophecy of how many years it would be from the time Judah was sent back to Jerusalem from Babylon to rebuild the Temple, until the appearing of the Messiah (Dan 9:25). So all Israel was in expectation at this time, that the Messiah would come in their lifetime. An He did!