Good post, Don. Writing reviews helped me a great deal. As you said, it does force you to really focus on the cigar.
One thing I did was after I read a review, I would actually seek out to smell or taste a frequently mentioned unfamiliar note. For example, the only time I eat caramel is in a candy bar. For me its hard to isolate, because the candy bar has caramel, nuts, and other things. So I bought caramel so I could identify the taste. I did this with cocoa also. I don't cook much, so I went in my wife spice cabinet, and I sniffed the difference between red pepper and black pepper. Little weird things like this helped me out. The challenge (and the fun) of reviews is finding clear language to communicate to others what I'm tasting.
It takes time to develop, but it does come along. Retro-haling, smoking slower, and rolling the smoke around my mouth all help me to taste more.