Welcome, wburns710!
I would echo much of what G55 said.
I think Unfinished Tales is a great work for "filling in the blanks" on some things a Middle-earth reader might wonder about.
As for the non-ME stuff, Farmer Giles is a personal favorite of mine. I see a lot of Bilbo Baggins in the protagonist there.
I also like Smith of Wootton Major, where there are again some Middle-earth parallells in a more "real" setting.
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