Well to start out, how do you properly light a cigar? Well try this:
Ideally you light a cedar stick with a match and use it to light your $25 Cuban cigar. -BUT- who carries cedar sticks or matches?
Matches are best after the sulfer and magnesium burns off but a lighter will also work, butanes better than BICS (they get hotter faster) on your $2 cigar, just toast the tip real good, DON'T SUCK IN THE LIGHTER FUEL, just lightly puff.
(no suck jokes please
Now, from CigarAficionado cigar 101:
HOW TO LIGHT A CIGAR
Lighting a cigar is not like lighting the tip of a cigarette or the wick of a candle--it takes longer. Light your cigar the same way you would toast a marshmallow over a campfire--keep the cigar above and near the flame, but don't let them touch. Burning a cigar directly in a flame makes it too hot. And, as with a marshmallow, you'll want to rotate the cigar so all parts of its tip are equally heated. Be patient, and keep at it until there's a glowing ring all the way around the cigar's tip. Once the cigar is lit, gently blow on the embers to create a smooth, completely rounded ash.
Then, raise the unlit end of the cigar to your mouth and take the first puff. The question is, which way to puff? Many aficionados blow the first puff out through the cigar in order to avoid unsavory flavors such as sulfur from matches or gasses from lighters. No one, of course, should ever apply more than one outward puff.
To Relight, or Not to Relight
Some purists think that it's shameful to ever have to relight a cigar. Realistically, even the best cigars will go out on those occasions when the conversation becomes so absorbing that you forget to take a puff for a couple of minutes. It's no worse to have to relight a cigar than it is to have to fish a bit of cork out of a fine glass of wine. It will generally take you less time to relight an already-warm cigar than it does to light one for the first time.
Do not, however, intentionally let your cigar die out and then relight it the next day. This will lead to stale, harsh flavors that will ruin your fine memories of the first few puffs.
If you have to relight a cigar several times, you may have a badly rolled cigar. Premium cigars are made by hand, not by machine, and they are made from organic materials that retain much of their natural, irregular structure and character. Despite dedicated quality control efforts, a substandard cigar occasionally makes its way to the market. Don't hesitate to bring a badly rolled cigar back to your tobacconist. Most will happily replace it.
Choosing Your Flame
Never light a cigar with a flame from a source that will alter the essence of your cigar. Using a candle, for example, is a temptingly theatrical gesture, but the burning candlewax can add an odd flavor to your cigar. So can the fluid from an isobutane cigarette lighter. Many smokers also object to the sulfur used in most match tips.
If you insist on using a candle or a fluid lighter, use it to light a strip of cedar, called a spill, and use that to light the cigar. If you insist on matches, try to get extra-long, wooden sulfurless ones. If you can't find them and are using regular, short matches, be prepared to use a number of them. Be sure to let the sulfur burn off before starting the lighting process and try lighting two at a time, so you get a broader flame.
Cigar lighters are the easiest way to get an even light. What makes a lighter a cigar lighter? A cigar lighter uses odorless gas, and often "fatter" flame, or even two adjacent flame sources, and adjustable flame heights.
Cigar lighters come in a wide range of designs and materials, so it will be easy to find one that's an appropriate accessory for your sense of style. Your first requirement should, of course, be performance. A good lighter, like a good pen, should fit your hand. The cap should open easily, and swing back so the whole flame is available for lighting. *