I have been smoking for a couple years now and I rarely buy a box. I do like the 5 packs a lot as it gives me a chance to buy different sticks with out to much cost. I really like variety and I have over 20 different brands and styles. I select what I want to smoke depending on the amount of time I have as well as the "heaviness" of the smoke. Sometimes you want the full body smoke, sometimes something on the light side. Hope this makes sense to you.
The best part about smoking more seriously the last year or two is that I've narrowed down what I like, dislike, and what I really love. Lately, I've been attempting to only buy and trade for cigars I really love! No more "everyday" cigars - I have plenty of those already. I have bought a few boxes here and there, but in general if I really love something I try to get at least a 5 pack or more. My problem lately is that the cigars that I really, really love are more expensive, and buying boxes really hurts.
I started off with a lot of samplers to narrow down my preferences. I'm at the stage right now where I will invest in a couple of 5-packs on stuff I've liked before. I'm not quite at the stage where I want to buy entire boxes. Like you said, there is so much stuff to try out there.
I can probably pull out a new stick from my humidor everyday for the rest of the year and every stick will be a new one to me. I have stepped up my smoking this year big time.
I used to do the sampler thing a lot and the lower level of my humi is still filled with a lot of onesies and twosies. My last several purchases have for the most part been boxes as I find favorites. AAA, La Herencia Cubana Oscuro Fuerte, Vintage 2002's. In some cases not a box, but buying enough of the DD to approximate a box quantity at a better price. Still like to try something new now and then but not actively seeking out new stuff. If I stopped buying cigars today I could go for years without running out.
I love smoking new things so I buy alot of samplers that are aimed at the flavor profile I like. When I first started smoking I just bought tons of different stuff to figure out what I liked. I do by 5 packs, bundles, or boxs of stuff I really like to smoke if Im not in the mood to try something new.
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