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I suggest going to a local cigar store, and looking for the Cigar Handbook. There's a few different books that go by that name (or similar names), but the one put out by Cigar Aficionado is very informative, and is such a beautifully made book, that it looks at place on the coffee table of any home. It will school you in how to select, store, light, cut, smoke and talk about cigars. It'll also teach you the growing regions, and the terms used.
Also, I'd definitely not recommend starting out with boxes. I have 7 humidors full of cigars, and never buy by the box, simply because I like to try new things, and find what I really enjoy. Unfortunately, most of the things I enjoy enough to buy a box, I can't afford a box of.
I use a double-bladed, self-sharpening cutter. I prefer it to single blade cutters, since it's a little cleaner cut. And I don't particularly care for punches at all, although they're sometimes necessary for cigars that either have too large a ring gauge to fit into a cutter, or have an unusual head, such as the Chisel (a new cigar with a chisel-shaped head).
As for lighting the cigar, you can use the cedar as suggested earlier (it's called a cedar "spill"). You do so by using a lighter (preferably butane) to light the cedar, and then use that to slowly light the cigar, being careful not to actually touch the flame to the tip of the cigar.
I personally find that to be a great hassle, so I use a butane jet lighter. Don't use a Zippo style lighter, unless you'd like your cigar to taste like lighter fluid. And it's best not to use a candle, no matter what you've seen in movies (airborn wax particles can attach to the cigar, and ruin the smoke).
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it's all about self-indulgence
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