In the first year of law school students learn that for every clear legal rule there always exists situations for which either the rule doesn't apply or for which the rule gives a bad outcome.

If the rule doesn't apply, it's not relevant in the first place. I doubt very much you can establish what a 'bad' outcome would involve in such a way that everyone would agree - and I don't see why your personal opinion on the matter should be of concern when we consider legal design.