Interesting topic, Tommy, and one I've been thinking about a lot lately.
In general, I smoke far more of what most people would consider "boutique" brands than "flagship" brands. That doesn't that they're not well-established or well-known, just that they're not the mammoth brands that had been around for years pre-boom.
Most of what I smoke these days, at least on any kind of a regular basis, have "Pepin" Garcia's, Pete Johnson's, Alec Bradley's, or AJ Fernandez' fingerprints on them. Part of that is because I like the work these guys have been doing over the past few years, and part is because I simply have not cared for the "Cuban-name ripoffs" that constitute most of the "established" brands that are out there. If I see a name like Cohiba or Bolivar or Partagas or Romeo y Julieta or...well, you get the idea...I generally avoid them because I've found them to be pretty blah in the past.
Now maybe that's because I associate something with the
name that is just not going to be there - you simply can't make cigars that taste like Cubans with tobacco from anywhere other than Cuba. I recognize the fallacy in that kind of expectation, but I just can't dismiss it.
I actively avoid certain "established" brands altogether. Most notable among that list are Arturo Fuente (bland, usually tarry, vastly over-hyped/priced) and Rocky Patel (no way can I keep track of all the lines with his name on them, so I don't even try), but there are others.
If I had to cite one example of an established brand that I enjoy, it would probably have to be Punch, and the Rare Corojo line in particular. Get some age on those suckers and they can be epic. The Hoyo de Monterrey Dark Sumatra line is another that I've smoked a bunch of and enjoyed. If you consider La Aurora to be an established name, then their 107 line (particularly the coronas) are excellent, as are most of the Preferidos perfectos. La Gloria Cubana is still on my list, particularly the new Rabito de Cochino.