Recall the scene in French Kiss when Luc teaches Kate to identify the flavors in the wine. He used an old school project, samples of herbs, roots, and other items that are in the soil and contribute to the character of the vineyards' grapes. Kate smells the lavender, drinks, and then can distinguish its presence in the wine.
I need such a collection of things in a tobacco fields' soil, and other influences that make their way into the leaf. Sadly, I can't afford to travel to Honduras, Nicaragua, and parts unknown, just to collect dirt and wood samples.
One characteristic of a cigar that I've been able to pick up on fairly easily is its spiciness, or lack thereof. The Vintage 1992 didn't seem to have the subtle pepper spice that I found in the Decade, and it had a touch of sweetness that I liked very much. This might be the simplest aspect of cigar tasting, the shallow end of the pool, so to speak.
In the meantime, I'll learn to distinguish more elements of cigars by smoking them, read what other folks think about 'em, and smoke 'em again. Gradually, I'll make my way out to the deep end.