I work full time in retail mattress sales (not the most romantic product, though lots of romance happens on them), and part time in marketing. When learning how to sell, then when learning how to market a product I had to learn what motivated people to buy. With the possible exception of some very basic needs people buy emotionally then reinforce it logically. Especially with luxury items, which really is anything we buy that we don't really need, or a nicer, more expensive version of a product when there is a less expensive option for the same product available. Most of what we buy we don't need and while we will work on the back end to justify it (logical reinforcement), the buying process on all these items begins with emotion. A Honda would get the job done, but it just feels better to drive a Mercedes or Jaguar.

Cigar smoking as a whole is a luxury. We all do it just because we like it. It makes us feel good to sit back and light one up. If it was just about smoking we would all be stocked up on the cheapest gas station cigars available. It's not just about smoking, it's about the experience, the taste, smell, draw, construction, but also about the presentation and the stories behind the products. It all works together to create that experience. It takes a better product to create a better experience, but also better presentations and better stories. All of those things cost dollars to create and the ones who are good enough to put it all together and convince me to spend $20 plus dollars on something I will turn to ash deserve more profits than someone who can only convince me to spend $5 on this soon to be ash product. If it were easy to do we would all be selling $20 cigars for insane profits.

My point basically is that as long as you are taking comparable products that have a difference in price and working to justify that difference by the matterial difference alone, you will be left scratching your head. And as long as you are only making practical, logical purchases that are void of emotion, you will likely not ever own much that you truly enjoy.