Question:

Why did Jesus pick Galilee as the place where his disciples would see Him?

Answer:  

Multiple reasons

1. The Pilgrim Feasts were over and it was normative for Galileans to return to Galilee until next Pilgrim feast 50 Days later (Shavuoth/ Weeks; Pentecost). By returning to His earthly home in Galilee Jesus was showing He had totally accomplished the Messianic Fulfillment of Passover and First Fruits which had to take place in Jerusalem. This is a little complicated to explain. Answers to such questions are usually found in the Torah. Only Jews who completed the two Pilgrim Feasts could return home. If someone became ritually defiled (by a touching a corpse or pagan contact or something inadvertant like a male coming into unintentional contact with menstual blood - all kinds of stuff; see for instance John 18:28) . If a Jew did not totally fulfill the feasts they had to remain in Jerusalem for a whole month of purification to observe the two paschal feasts Pesach and First Fruits. By Jesus going home He signified He achieved the fulfilment as the Paschal Lamb and as The First Fruit (1 Corinthians 15:20).
2. The eschatological typology of Peter jumping overboard from a fishing boat could not be achieved in Jerusalem but required the Sea of Galilee (I once explained this typology at a bible study at the branch).
3. He had to totally fulfill the Galilee prophecy of Isaiah 9:1 about gloom and anguish being over (because  He was risen) which was previously only partially fulfilled in Matthew 4:15 because the gloom and anguish of His crucifixion were still to come. Only after the resurrection could Isa. 9:1 be fulfilled which had to take place in Galilee.There is a deep eschatological meaning about the term in Matthew 28:16 "to the mountain Jesus had designated".