IMHO, most 'expensive' cigars aren't worth the msrp.
Having said that, there are some xlnt smokes that are
out of my usual price range. I stopped buying special
smokes for Xmas/New Year because it's too cold outside
to enjoy them. But for my vacation and b-day I try to
get a PAM or ESG or Fuente Anejo. All xlnt smokes.
My regular rotation is San Cristobal, La Riqueza, AF Hemi
maduro and Oliva MB3, which are 'expensive' for some people.
But I only smoke 2-3 per week, so it's easier to stay within
budget.
For me, the Oliva MB3 tastes very similar to a PAM, so that
gives me a PAM profile for a reasonable price.
You'll just have to try the 'expensive' sticks when you can,
and determine which are worth the coin to you. I got some
GOFs to try, recently. I can hardly wait, for warm weather,
to try them out!
Graycliffs are much more affordable on the Devil's Auction
site.
Chemyst