(5) Tree Line
We're actually being serious, Shmoopers (and we're never serious). This text is actually not that mind-fryingly difficult. Unless you're reading it in the original Ancient Greek. In which case: psshhh. Good luck to you.
For the first-time reader, probably the hardest thing about Homer's Iliad is its language. Even the most up-to-date translation – those by Robert Fagles and Stanley Lombardo use probably the most contemporary phrasing (Lombardo especially)—is still going to have a lot of repetitions and lengthy who-killed-whom-and-how battle scenes that sound just plain weird to modern readers.
On Shmoop, we quote from the 1950's version by Richmond Lattimore, which is a bit harder than those, but which has some advantages that make it worth using. (Every line in Lattimore's version matches up exactly to its counterpart in the original Greek; its quirkiness actually gives a good sense of what the original feels like.)
And once you get past the weird cultural details (reading the introduction to your edition will help), the poem is extremely accessible. The characters are vivid, and every reader will find someone to identify with. By the time you start thinking deeply about the book's themes of life, death, and fate, it won't feel like a chore—you'll be hooked. We guarantee it.