I even heard one preacher go so far as to say that shepherds tended to be dishonest and often stole from others. I beg to differ here. Shepherds had to be trustworthy. After all, they would risk their lives to protect the lambs of their masters. Many times they would have to face off with lions and other wild animals to protect the flock. When they put the lambs and sheep into an enclosed pen, they would lie down across the opening so that anyone trying to steal them or any animals trying to kill them would have to get through the shepherd first. It is no wonder that Jesus referred to himself as the good shepherd.
The shepherds would also be the only ones outdoors at night when the angels made their appearance. Unlike people in the city, they would not be wrapped up in their own lives with their doors and windows bolted shut. While they were not intentionally watching for angels, they were watching, and thus were an ideal audience for the most glorious choir this world has ever heard.
Our earthly customs would have dictated that a birth announcement like this would have been made to the king of the region. The magi who were seeking for Jesus nearly two years after his birth expected the king to know about his birth so that is where they when when they arrived in Judea. When he found out that a king of the Jews had been born in his kingdom, he did not go to welcome the king. No, Herod was not the compassionate kind. Instead, he had his soldiers kill every male baby among the jews in an attempt to kill Jesus. It was only because an angel had warned Joseph and Mary in time for them to escape to Egypt that they didn't kill Jesus too. If the angelic chorus had gone to Herod's castle to make the announcement, he would have tried then to have Jesus killed. For the angels to make their announcement to commoners made much more sense from a practical point of view as well as to show his humility.
Let us be like the shepherds, paying attention when God sends His message of good news, and telling others about that good news.