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[cigar coach]

I have also only been smoking cigars for about two years and had the same question a few months in. What I settled on was trying a lot of different things and keeping a notebook with a review of everything new that I try. I find this keeps me from forgetting if I had this or that previously. It also reminds me of my initial impressions of the cigar so I don't buy something for a second time that I really disliked the first time out. The Premiums are usually pretty good but the one that gets a lot of press that I can't seem to find a vintage that I like at all is Gurkha. I have settled on a regular rotation of:

Rocky Patel Sungrown
Torano Exodus Silver
Oliva Serie G and Serie O (G is a bit too full bodied for me)
Hoyo De Monterry (various vintages - like them all)
Don Tomas Maduro
Cuesta Rey Cento Fina 55 (these are as full bodied as I
tend to like)
Ashton (various vintages - like them all)
Arturo Fuente (various vintages - like them all)
Gispert
La Gloria Cubana
Perdomo Habano (strong to my palate like the CR-55)


Hope this helps.