Why Sauron didn't know about The Shire. March 27, 2032

The reason Sauron did not immediately send his minions to The Shire, was he didn't know anything about it. That is the simplest explanation. But to make it longer, was because Hobbits and the people that lived in the nearby towns like Bree, were not much involved in the world, at least by that point in MIddle-Earth history. If it was somewhere more involved in the world, he would have sent orcs after it. That was how he found out about Isildur possessing it. Gollum spent all those years, hiding in the Misty Mountains, keeping to himself. The Hobbits seemed of little importance, so it was Gollum telling him it was there, that finally made him aware of it. It was just then when he was able to gather the Ringwraiths, and then send them to The Shire, which was why Frodo had to leave. It was why he is quest should not be generally known, because if he was Sauron would have found out. He never knew about the Fellowship, and when it scattered, Aragorn came out of the shadows, scaring him into not looking for Frodo. 

Though I would have preferred if Frodo was more involved in the stories action, and participated in at least a few battles, but if he did, Sauron would have discovered him. The thing I like about Hobbits, is they are good natured and optimistic. Gandalf said you can learn all there is to know about their ways in a month and after a hundred years they can still surprise you. Though Aragorn is my favorite Lord of the Rings character, and favorite fictional character period, I have to say Sam is definitely the purest character in the saga. He starts off a little naive, but gains intelligence and wisdom on his travels, and would die to make sure his best friend survives. Though Frodo was the Lord of the Rings character aside from Aragorn, as inspiration for Jack Stamper, I feel like he is starting to relate more to Sam. And if you want to learn more about him, you can just read my books.