Pride and humility are often opposed to each other. Some regard humility as the virtue, contrasting it with pride, which is characterized as involving vanity or arrogance. Others praise pride, and characterize the humble person as self-effacing, servile, and resigned, lacking in proper self-respect. However, I don't think that humility rules out self-respect (or even "taking pride in a job well done" or being proud of our children, and so forth). I tend to think of humility as a matter of keeping in mind one's dependency on others, and on other factors beyond one's control, being mindful of one's limitations and fallibility, on the work that is yet to be done, or improvements to be made, but not as celebrating these facts about oneself, or of being so severe with ourselves that we resign to our fates or waste our talents or fail to stand up for our principles. (See, for example, Kupfer and Snow on humility.)
On the other hand, there is a kind of pride, which is primarily a form of self-respect, which doesn't seem to exclude humility (or: which doesn't entail either vanity or arrogance). This latter character is the kind of pride which Tara Smith attributes to the person who, in virtue of (sound) moral principles, won't do things that are "beneath" him, won't compromise on his values (unless he can be shown his mistake). This person is autonomous in the sense that he or she doesn't seek the approval of others (as some vain people might), but this needn't entail any kind of dismissiveness of others (who have legitimate claims). Let us call this a form of "proper pride" and allow that this virtue has an axis along which there are excesses and deficiencies.
I'm thinking that virtuous humility can be seen as falling along a distinct axis which intersects with this kind of pride, and that there is virtue in both orientations. (Not that "proper pride" and "proper humility" are synonyms.) The following (provisional) graphic illustrates this, and I've given names to non-virtuous folk who might be seen as failing in terms of both pride and humility. (The virtues in both cases would be at the intersection of the axes.) Sorry that the print is a bit small. (Click the image to see it full size.)
As for the problematic characters, who have neither proper pride nor proper humility: the "dogmatic servant" would be someone who is "too humble" in the sense of having little or no self-regard but also "proud" in the sense of uncompromisingly serving his or her master (a person or a system of value)--a henchman of sorts. The "spineless follower" also has little or no self-regard, and is "spineless" in the sense of having no core values around which to cultivate a self-respecting identity. Such a person would follow the "fascist" into the fire. The "fascist" is both self-inflated and goes beyond reasonable self-respect in being utterly uncompromising and fully separates himself from others, rejecting all help and criticism. Such a person has no ears to hear others, no eyes to see them as others. Finally, the "insecure attention-seeker" is a kind of vain person who depends on the praise and attention of others to fuel his own view of himself. Like the "spineless" person, he lacks any sense of principle.
It seems clear that these are distinct types of characters (and presumably there could be characters who find the mean along one axis but not the other), and so I think the positioning of these two axes does some real work, and that suggests that pride and humility are not (in every sense) opposed. This conflicts with some of the ways we use both terms, but if there is something in both pride and humility that seems good, and character traits that both oppose which seem vicious, then perhaps this suggests how to reconcile forms of both pride and humility, in order to reveal where the virtue in each one is.
This idea just hit me today, so again this is provisional, and I humbly submit it for comment and critique. (Though I also provisionally take some pride in what I hope I can show to be a good idea!)