I had a friend mention to me recently that he was interested in praying the Liturgy of the Hours (Divine Office), but he was frustrated because it is so complicated and he doesn't know where to begin. I know exactly what he means. I had to start reciting the Office when I joined the Third Order Dominicans, and I also found it very frustrating. The Office was simplified after Vatican II, but I still found plenty to complain about.
So for all those out there who are interested in making a habit out of reciting the Office, here's what you need to succeed:
1. A Breviary.There are one-volume breviaries, but I use the four-volume set, as it is more complete and easier (in my opinion) to use. You can get the whole set, or you can buy it one volume at a time for about $35.00 per volume. If you want to take that approach, we start Volume I on Saturday evening, when the first Sunday of Advent officially begins. Also, you should get a cover for your breviary, with pockets and zippers. Everybody who prays the Office regularly accumulates holy cards, slips of paper, etc. in their breviaries, and the zipper cover keeps all this stuff from falling out.
2. A Cheat Sheet.This is probably the most important tangible object after the breviary itself. New breviaries usually come with the current one; otherwise, you can pick one up for a couple of bucks. Sometimes the cheat sheet has mistakes in it, but don't concern yourself with that in the beginning. Do not succumb to pride and be ashamed to use a cheating aid: it's more important to do it right than to be an instant master.
3. A Teacher.The Office is really not that difficult, once you get the hang of it; but you're never going to figure it out on your own. Why? Because, for one thing, you have to skip around a lot in the book, especially on big feast days and solemnities, and you'll get lost without help. Also, the breviary doesn't remind you to do certain things, like saying the "Glory Be" after every psalm and canticle, so you need somebody to point out these things the breviary just assumes you already know to do. Even under The Redoubtable One's tutelage, it still took me a good year to get the hang of the Office, in no small part because I didn't have enough of the next thing you need to become competent at it:
4. Diligence.You need a lot of stick-to-it-iveness to pray the Office. I frequently got frustrated and gave up for periods of time before I got the hang of the Office, so it's a good thing the Rule of my Order doesn't bind on pain of sin. Do not, however, follow my poor example.
Also, remember that the duties of your state of life come first, even if you are a member of a Third Order. For those of us who live and work in the world, it is not possible to pray all the hours, and we shouldn't try if it conflicts with our responsibilities. Morning Prayer and Evening Prayer are the two most important hours, so if you plan on saying the Office regularly, try sticking with those. The Rule for Dominican Laity, as applied in my province (the Western Province, Holy Name of Jesus) prescribes Morning Prayer, Evening Prayer and Night Prayer to the extent possible. (The Office of Readings may be recited at any hour.)
Good luck in praying the Office, and always remember to seek help when you need it!