#1 buy at least one book on the subject (ABC's of reloading, Lyman, Lee, RCBS, Hornaday, Sierra or another such).
Read it at least once.
Find someone near you that reloads and look, listen and learn from experience. You may even find someone that will let you use their equipment and your components to get yourself started. There is a bit of trial and error when it comes to purchasing equipment. Learn from other's trials and errors as much as you can.
The big question will start off with how much are you actually going to load?
If you are only going to load a few hundred rounds a year, a single stage press will be fine for you. RCBS, Lyman and Lee are three very popular and good quality brands.
If you are going to load a few thousand rounds a year get a Dillon RL-550. Don't waste your time and money on a Lee progressive.
The sky is the limit and you tend to get what you pay for. Inexpensive Lee starter presses are decent if you are a low volume loader. Dillon 1050's are primo and will crank out huge numbers of rounds in short order.
If you read the ABC book or the Lyman book you will get a pretty good idea of what equipment is needed. Press, dies, scales, powder measure, trimmer, de-burring tool, case polisher, the list can go on ad-nauseum.
I use, Lyman, press, RCBS .223 Dies, Lyman powder drop, Lyman tumbler, Forster case trimmer, Lee handheld primer loader, CCI primers, Hogodon BLC2 powder with Sierra HPBY match, 69 grain. But whatever makes u happy, take ur time, do a good job and in return u will get a good looking, safe load.
Go to lockstock.com, cheap reloading supplies. I bought a press, powder dump, and, dies. My father in law works at hornady making bullets, and lockstock.com was cheaper than he could get it. The only reason I liked the hornady press better was their lock-n-load bushings that go on dies. When you are trying out different loads, they change out a lot faster.
I owned RCBS years ago and it was GREAT! But now, I'm in your position and want to re-load my AR only. I'm considering the "Lee's 5oth anniverary reload kit" from Cabela's for $85. That includes press, powder measure, scale, and few other access. All you'd need is a set of .223 dies for $13 (Lee). If you buy before 12/8, Cabela's has a $20 off coupon for orders over $100. .223 is a small cart and doesn't require the muscle of a large cal belted mag. It is "O" frame design so should work OK on .223. This is a starter and not for serious shooters loading multiple calibers. It does however have the quick change breech blocks (2) included.
ClevelandRocks, you also forgot to mention that there is not one kit on the market that includes everything needed to start reloading, especially when we're talking rifle brass. He will also need a measuring tool such as calipers to measure case length and also a case trimmer (very important). Since we are talking 5.56, the primers are crimped (LC, WCC, etc), therefore a swage tool becomes very helpful since the crimp needs to be removed before another primer can be seated. Rifle brass must be lubed prior to resizing, more cost, not to mention a good tumbler and media. I would suggest you buy a book first to see all thats involved. I would reccomend that to anyone getting started. Generally, that is where most of us start.