I've only been smoking since about August of last year and one of the resources that helped me tighten my grouping has been the "
Famous Flight Club" samplers at
famous-smoke.com.
They have a bunch of samplers organized in a grid by strength and price point. I might quibble with how they categorize a couple things, but all in all they really helped me learn how to recognize key elements and understand what I liked about which cigars.