While the Landmark edition may not be the best translation it does come with a wealth of maps that help. Is there a version of the Iliad that has marginal notes (like a study bible?) that help the reader?
For an exciting retelling of the Iliad, listen to the Trojan War Podcast. It is a good start. Some versions of the Iliad have very boring notes, but this podcast is great and my son listened to it twice through all the way (at 12 and 14). Plus the Iliad doesn't cover all of the war, but only a bit of it, and the podcast covers more of the before/after to the war.