Some of the difficulty might be because the availability heuristic is causing us to focus on things which are relatively small factors in our global preferences, and ignore larger but more banal factors; e.g. being accepted within a social group, being treated with contempt, receiving positive and negative "strokes", demonstrating our moral superiority, etc.

Another problem is that although we seem to be finely attuned to small changes in social standing, as far as I know there have been no attempts to quantify this.