[T.G]

I have no personal experience with flavored cigars, but I do buy and send a lot of them over to our deployed military units. The most popular seems to be the coffee flavored ones.

For traditional cigars, Macanudo Court, Portifino and Hyde Park are popular (all skinny cigars), El Rey de Mundo Cafe (small), JR Ultimates, La Finca, and Padilla maduro pigtails.

I personally feel you can't go wrong with the JR Ultimates. There are probably a hundred different combinations of vitola (size/shape) and capa (wrapper leaf) to pick from. Big, small, light, dark, strong to mild, that line has just about everything. And, I've never had a bad one.

Fuente is another option, I would avoid the brevas ("It's a boy/girl/human/thing") and the curly heads, but their long filler stuff is solid. It might take a few times smoking them to "get" their higher end cigars - Hemingway, Don Carlos, Opus X, Anejo, etc.
The Anejo is probably the easiest to "understand" of the high end ones, but it's strong.

Padron, there's another company you can't go wrong with. But they are stronger.