Some great responses so far...I too prefer quality over quantity, however, I have found that a high price point with a legend attached does not always...in fact, not too often in my experience...leads to an outstanding smoking experience.
Lemme put it to ya this way...a few years ago, I walked into the acoustic guitar room at a music store, and I played all the acoustic bass guitars (ABG) they had there. The one that played the best was a Martin. No surprise there. It was $1200. The second best was an Olympia...a second line of the vaunted Tacoma...the difference was small, in my experience. The price on this one was $400. Was the difference in performance worth $800? Oh heck no. Not even close. So I bought the Olympia, paid big bux for a hard shell case, still have both of them.
Now then, if I was at a different level of musicianship, where the small differences in the performance and sounds of those instruments made a difference, or if the world I played music in was the sort that looked down their long noses at a cheap Olympia, but accepted the Martin as being pretty much the top of the marque...which it is...well, the extra money woulda been well spent. But the difference to me simply was not worth it!
That's the way I approach cigars. Okay, I can pay almost $28.00 for a Padron 1926 at my local B&M...and it's an outstanding cigar, no doubt, one of the world's best. Nobody will look down their nose at me when I fire one of them puppies up...but I don't care. I went out a bought about fifty of them Devil's Ink on special for about $2.49 each, and man...do I enjoy them! For less than nine percent of what that fine Padron costs.
So which gets the nod in my world? Yep...the less expensive stick...Sounds like there are some folks who are with me on that, but I'd sure like to hear from some others who disagree as well...always interested in points of view...