Why no one questions Gandalfs background

Though, I agree that the hobbits may be seeing Gandalf and much else beyond the Shire as simply lumped together under "other" and only really begin to want to dig deeper once they've already begun to learn more.

This has been my thinking as well. Hobbits universally regard outsiders with varying degrees of suspicion, whether it's odd and suspicious like the Bree-land hobbits or odd and stupid like the (apparent) stereotype of Men. The Gaffer even regards hobbits from Buckland as queer.

Given that, it wouldn't be at all odd to simply lump this apparently magical outsider on the same spectrum. Since Gandalf has apparently been involved in Shire business since time out of mind without any truly significant problems, it's not unreasonable for them to regard him with the same sort of cordial suspicion accorded to other residents of the Shire.
 
I expect that the Butterbur family has known Gandalf for hundreds of years. I can just see the scene of little Barliman hearing stories about Gandalf from his grandfather.
 
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