Gosh, I am almost ashamed to admit that I have a humidor and about 6 boxes aging away. I don't smoke all that often, and like my home-brew, give more than a few away. I am pretty careful about when I smoke if I am going to be judging in the next week or two - or packaging for a competition soon.
I am a gigantic fan of Rocky Patel's offerings. Met his son once and he walked me through how they age their bales and particularly focus on minimal residual ammonia, along with other undesired chemicals. I was already a fan, and his passion helped to cement my loyalty there. Their 1991 and Decades are some of my favorite smokes. Prices have been rising pretty steadily, so happy I have a couple of boxes aging already.
Like mentioned, seems that a good experience helps to elevate a cigar. Early on, I bought some Montecristo #2's and sat outside on a hot and humid evening drinking a great tequila over ice. I couldn't afford the cigars or the tequila at the time - so it was a real treat.