1. Attraction and intrigue with "the leaf".
Enhancement of the moment - I light up when I want to, where I want to. Because I want to take wherever I am at that moment and turn it into a more relaxing, enjoyable time. That may be after dinner, on my deck in the summer, by the campfire, after a business dinner or lunch, and in the vehicle traveling. When I light up I am "large and in charge" and my wife recognizes the mood, as do my children and my co-workers when we are out and about. When I light up after a business dinner, it's a signal to my staff that I'm about to hold court. My kids know the same signal. My wife sees the stress of work melt from me after a couple of puffs on a good smoke. So cigars are an important part of my life, ranking up there with food, socializing, relaxation.
2. What makes a good cigar: It starts with the smell pre-light, and the heft (I prefer larger ring cigars). I like a label with some character, as well. The amount of tobacco in the stick and the relative humidity affects the heft and odor, as does the age. The color is uniform, the leaves have some physical character. The cigar lights easy, burns evenly, and the more snow-white the ash, the better I like it. I like one that starts with a kick, then relaxes slightly to a body that you can feel in your stomach and head as the smoke progresses. Lots of billowing smoke, easy draw, stays lit, and you can smoke it to a tiny nub without it getting tarry or bitter.
3. I pay what they are worth to me, not what the manufacturer thinks they're worth. Thus I happily pay retail for a Hemingway Classic, would be willing to pay twice what I pay for Padrons, and won't pay half of what they want for some other "super premiums" that I have tried and found thoroughly "average."