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Lighting is the most important part. In order to light a cigar correctly, you have to "warm" it. To do this, light your match or lighter (thalakos is right, if you use a butane lighter if you don't use a match), hold the cigar at an angle over the flame, and rotate it slowly a few times. If you really want to do it right, never let the cigar touch the flame. Then put the cigar in your mouth, hold the end over the flame, draw and rotate. You should get an even light then.
If you're smoking outside, wind might be a factor.
btw, Jorgelito, the only widely distributed, non-rare, non-vintage stogies I can of over $20 bucks a cigar (at least in the States) are Hemmingways. I was wondering what brands you were refering to.
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