Fingolfin II you wrote that in his conversation with Gildor
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Frodo is gradually beginning to learn that there is more outside the familiar square of the Shire and that he- as well as other hobbits- have to learn how to deal with the outside world and leave their comfort zone.
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The irony of their conversation is precisely that it is taking place
inside the Shire. So there is much more inside their familiar world than they are aware of. The "comfort zone" that they live in is explicitly not a geographical one with impermeable fences and borders, but a state of mind. If you are aware of Elves (like Frodo) and/or receptive to meeting them (like Sam) you have a shot at meeting Elves
in your own backyard! However, it apparently works the same way with the dark and dangerous things: Black Riders are inside the Shire as well. So while I agree that there is a definite sense of inside and outside, us and them, in the Shire, the line between these realms is clearly drawn only in the minds of the Shire's residents -- well, not Frodo's, and after this meeting not Sam's either: the first step in each of their educations. (For Sam, that there is a whole world of experience beyond his own (Elves)? For Frodo, that this world of experience contains darkness and despair (Black Riders) as well as hope?)