Wilcock’s edition of the Iliad is good and more or less up-to-date.
http://www.amazon.com/Homer-Iliad-Books-I-XII-First/dp/B00866IF4I/ref=sr_1_1?s=books&ie=UTF8&qid=1452539322&sr=1-1&keywords=wilcock+iliad
There are even more up-to-date and generally excellent editions of individual books in the Cambridge Greek & Latin Classics series.
http://www.amazon.com/s/ref=nb_sb_noss?url=search-alias%3Dstripbooks&field-keywords=cambridge+greek+and+latin+classics+homer
Benner’s Selections from the Iliad is a good older edition, with footnotes, rather than endnotes, including unfamiliar vocabulary. It includes most of the Iliad and in particular the key sections, and you can buy it used at reasonable prices. (Older used printings may be more legible than the paperback version currently in print.) But you’ll want to supplement it with more up-to-date readings–there’s been a lot of scholarly water under the bridge that is helpful and illuminating since Benner was published (in fact, a revolution in our understanding the Homeric poems).
http://www.amazon.com/Selections-Homers-Iliad-Rogers-Benner/dp/0806133635/ref=sr_1_1?s=books&ie=UTF8&qid=1452539969&sr=1-1&keywords=benner+iliad
I haven’t seen this myself, but a number of people seem to think highly of this series, which is aimed at beginners:
http://www.amazon.com/Homers-Iliad-22-Vocabulary-Commentary/dp/0984306595/ref=sr_1_1?ie=UTF8&qid=1452541962&sr=8-1&keywords=steadman+iliad
Also, this:
http://www.amazon.com/Odyssey-Bryn-Mawr-Commentaries-Greek/dp/0929524667/ref=sr_1_26?ie=UTF8&qid=1452542240&sr=8-26&keywords=bryn+mawr+commentaries
By all means, equip yourself with a copy of Cunliffe’s Homeric Lexicon. This is an essential resource for reading Homer–very reliable, and it will make the task of looking up words much easier than using a larger dictionary. The edition currently in print is a revised edition, but the revisions seem to consist of adding proper names, which isn’t particularly useful.
http://www.amazon.com/Lexicon-Homeric-Dialect-Expanded/dp/0806143088/ref=sr_1_1?s=books&ie=UTF8&qid=1452540061&sr=1-1&keywords=cunliffe+homeric
A used hardbound edition will cost you more, but will last a lifetime, or as long as you are reading Homer, whichever is longer.
Homer will seem very difficult at first, with lots of obscure vocabulary and strange forms, and in the initial stages will require some hard work, but it won’t take too long before the oddities become familiar. It’s actually easier in many ways than just about any other Greek, including the NT, because the syntax is for the most part quite simple.
Learn how to scan and read metrically, whether aloud or silently. Again, this is something that seems quite daunting at first (assuming you haven’t studied Latin), but it’s by no means difficult, and if you try to work out the scansion 10-20 lines a day for a month or so, it should become second nature.
Good luck, and I hope this helps!