During the 90s, I was really into cigars. I got into it my last year in college, just before they started getting super trendy. I bought many singles from cigar shops, but mostly boxes from JR Cigar. Back then, they had a forum (like this) which told you the real brands which were re-labeled under their Consuegra (Connie) label as factory 2nds. I went through tons of El Rey Del Mundos, Hoyos, Belindas, etc. But they were young cigars, so I build many tupperdores (tupperware lined with cigar box cedar with humidifier), and aged them for years before smoking. By 2000, I slowed way down and now only smoke a few each year while outside. For some reason, they just don't taste as good to my 44 year-old taste buds.
One thing you have to realize is that cigars are like wine. What was good last year, may be crap this year. They're a natural product. Some are great, but the next can draw tight and be harsh. I learned to stick with corona/toro-ish sizes, because larger varieties tend to more inconsistent. Once you read a good review about a cigar in a magazine, it's too late to buy them - as they are now probably using different tobacco vintages. The aging environment is a big factor. Also, way too many crappy producers got into the game, diluting the product and making it difficult to find consistently good products. Plus, taxation got out of hand. I used to purchase Macanudo Hyde Parks, Arturo Fuente Hemingways, Henry Clay Brevas Las Conservas for about 2 bucks each. Now, you're lucky to find them for $10! To me, that's insane for a product that may be crap. I don't even recognize most of the fake-old school brands in the shops today. In many cases, investors bought the old names, or made up some cheesy names, bought some tobacco or simply slapped a label on an existing cigar and are in-business. I find the younger dudes working in my local cigar shops are full of shiite too.