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In a loose comparison between the Shire and our world, it strikes me as odd (sort of) that people can be dissatisfied with an imperfect world and at the same time be dissatisfied with a perfect world. In an imperfect world there is too much suffering and hardship and in a perfect world it is too boring. It sounds like we are doomed to dissatisfaction.
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I don't think that is quite the case
. At least, I hope not. Many humans (and hobbits) would prefer excitement at certain times and peace and qiuet at others. It has to do with the stages of one's life, in addition to your upbringing and environment.
Example: Bilbo. He was raised in part by his Took mother and her relations, which gave him a strong desire, and eventually a push, to go on his adventure.
Of course, we can't ignore his Baggins side either, because what does he do every time he has a free moment? He thinks about his armchair in front of a roaring fire, and eggs and bacon.
(Not that I blame him. Cram doesn't sound too appetizing.)
But after he gets back home, he doesn't settle down and try to regain his neighbor's respect. He starts going on long hikes, visiting elves and dwarves and rangers.
He does this because he has had a taste of something more, something different than what he had growing up all his life.
So he's not totally dissatisfied with the Shire, it is just like he said:
"...I am very fond of it, and of all the dear Shire; but I think I need a holiday."
So while comfort is all very good and well in its own way, adventure is a lovely thing too.