WRT the wine example, I've always noticed that, for those averse to spending money on wine (aka me), the second least expensive was the predominate choice. You want to minimize cost, but not appear "cheap."
My friend was just about to get DSL from Verizon and selected the "medium" package for $29.99. I asked what they needed the Internet for, and sure enough 1Mbps down / 368Kbps up would have been fine (this was the "small" package for $19.99). I told them that they could always upgrade if the "small" didn't do it for them.
this sounds quite logical but I'm curious if anyone here has done some A/B tests on it and would want to share