I like blind passes, but it's hard to do it dollar for dollar. You could tell everyone to put in one excellent cigar, one above average cigar, and one average cigar, but that doesn't really solve the problem because someone might pull three average cigars from the box when it comes to them.
An alternative is a kind of "round robin" pass. Geek 1 sends a blind package of 3 or 5 cigars to Geek 2. Upon receiving the package from Geek 1 (or even better, the sending could be done all at once, to speed things up), Geek 2 sends out his own blind selection of 3-5 cigars to Geek 3, and then begins to smoke and try to guess the 3-5 cigars from Geek 1. Geek 3, meanwhile, sends cigars to Geek 4, and so forth, with the last Geek sending to Geek 1. The benefits of this are (1) it's quicker, because you don't have to wait for the box to arrive, and (2) everyone gets 3-5 sticks that range over the spectrum.