When I first started out, I would buy 2-3 sticks if I wanted to try a new cigar, so I could get a good feel for it. One stick was too few for me to base my decision on, so I would always buy a couple.

I still do that for new things I am trying. For sticks I know and love, I buy them by the handful, but rarely by the box. I have made box purchases in the past but only when I get a great deal. I don't really have the room to store hundreds of cigars so I have to be careful not to buy too many.