I do think high school is the exact wrong time to read... [The Hobbit]. When you're younger you can be charmed by the world and bumbling little Bilbo, and when you're older you can see the interesting things Tolkien is doing with the larger & implied structure. But high school is exactly when Bilbo will read as the narrator condescending to the reader, and the whole thing will read as a loosely-strung series of random adventures. Which it's not.
As I read this, I couldn't help but agree - I've re-read JRR's work at several different ages, and each time found something new and different to take away with me.
It could be something as simple as the advance of my own understanding of the world - but, I've found, it hardly applies to all books. So, I was just wondering if any of you have discovered a similar phenomenon with certain authors/books?
As another example, I'll give you Heinlein. I started reading RAH when I was about twelve or so, and at the time found his work to be good 'action/adventure' novels. To this day, however, I can pick up any of his works and find new depths to his writing; always there to be read, but unrevealed...