To start with a practical scenario: I've got a small assortment of fine Cigars (e.g. Oliva Serie V), but have no clue when it would be appropriate to smoke them because my level of experience is nowhere close to matching the quality they offer.
Starting from practically zero Cigar experience, how far into my schedule should I plan on breaking out a decent Cigar? And How do you count Cigar Experience?
-Total time with a stick in your mouth?
-Variety of Tobaccos smoked?
-Maybe Learning to manage a Humidor? (How far can an affordable Cigar be elevated?)
At what point should a person experiment with even more expensive Cigars? (if ever)
When was your "Aha" moment, when the Cigar game made sense and you specifically found one thing you enjoy over another?
I only smoke what I would consider very expensive cigars....Davidoffs in particular; box price of 20 usually anywhere between $475 and $700, so I take great care in scheduling my smoking time around one.
To answer your questions in order:
1. Total time depends on a lot of things, most important of which is the ring gauge...the thicker it is the longer it will take (obviously length too, but not as much as ring gauge). The ring gauge of my cigars I prefer to be somewhere around a 50/52 or so. My cigars take roughly an hour to smoke with the stick in my mouth about 50% of that time which is probably more than most people, but Davidoffs are such high quality, it's hard not to chew on them while smoking.
2. Not quite sure what you mean by that second question. Cigars have 3 basic components, filler, binder and wrapper. Most of the time in quality cigars the binder and filler are the same but different from the wrapper--and wrappers are usually some sort of Connecticut wrapper in the milder cigars (like a Davidoff), but many times all three are different, especially in lower quality cigars (by different I mean anything from source, to growing technique, to curing...far more complicated than pipe tobacco for sure).
3. I used a humidor for decades until dependable Bovida packs have come out. Since then I just throw 1 small 69% RH pack per 5 cigars in the box the cigars come in, and that seems to be perfectly fine for keeping them up to about 5 or 6 months (like I do...I go through about 2 1/2 boxes a year). Humidors are a pain and I would now avoid using one if I were you unless you plan on having an assortment of singles...if you are just buying whole boxes at a time, Bovedas in the box they came in works fine.
4. I've tried dozens upon dozens of cheaper cigars, but the $30 cigar, so to speak, has always just been so much better, I can't even get through 1/3 of a cheaper one these days without gagging and throwing it away. So to me it's always been worth it to invest in more expensive cigars, but that's just my opinion. My son can smoke cheaper cigars without an issue, but I never could. Really in the end, it all just depends on how deep your pockets are; to me, cigars are like investing in the markets, at some point, you have to be able to sleep at night.
5. Never really had an aha moment...I've always enjoyed smoking cigars and pipes.