Hey Rob,
I've heard great things about the Vegas show, but have yet to attend myself...will work on correcting that, though. The Chicago pipe show is May 5 & 6, and is usually around the same time of the year, each year...biggest, and since I live in the Chicago suburbs, I've been going there regularly for the last 15 years or so...I usually go on Wed or Thur, and guys start arriving earlier in the week than that.
Not so sure about the analogy of flavored tobaccos comparing to flavored cigars. I'll smoke a cherry or vanilla blend occasionally, and at most, I'd say there's not much more than a hint of the flavoring. Flavored cigars IMHO compare more to flavored hookah tobaccos. Funny thing...the Chicago pipe club meets at a tobacconist, and a couple of months ago, they sold a blueberry flavored cigar, and the guy fired it up in the store. The whole store (it's a fairly large tobacconist) almost immediately was overwhelmed with a strong chemically/blueberry smell. Within minutes, the owner told his employees that going forward, they can only sell more of these to customers who agree not to light them inside his store.