I went to Iwan Ries with a friend of the family as a kid,
I was smoking Macanudos in HS,
when I went to the CBOT my Mom's friend took over Jack Schwartz cigar importers, and his store was next to the CBOT, and then later in the CBOT. He really showed me how to underdstand the qualities, like wine. As you said, anyone can get a smoke for $20, someone with a good nose can find the same tobacco in a $4 stogie, he showed me how.
You should try pipes. It's less time, less invassive to the palate as well.
I know it seems gay (did Huge Hefner give you that pipe) but I like it.
"Those who do not learn from history,
are doomed to repeat it."