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Originally Posted by Charlatan
Save the Silmarillion, the Lost Tales and all of the other histories until after you have read the Hobbit and LOTR.
It's difficult to appreciate them without first having the more fully realized stories. The reason they are a little bit harder to read isn't so much that they are just dry, it's that they stories and notes that Tolkien had that he never finished writing. His son brought them together the best he could.
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Agreed. Definitely start with the Hobbit, and then on to Lord of the Rings. The Silmarillion is like the Bible of Middle-Earth. Sometimes it feels like a long list of who-begat-who.
As for editions, go to your local used bookstore and peruse their shelf of Tolkien books. You'll find an edition you're satisfied with, and for a good price. It will also give you a chance to look at the other books, like the Lost Tales and the Histories.
I currently own the Lost Tales, the Silmarillion, the Hobbit, two three-book editions of the Lord of the Rings, and a compendium edition of the Lord of the Rings. I'm trying to build a collection of Tolkien books.