At ArcGIS 10 there is a sort tool that can do spatial sorts, but it currently requires an ArcInfo licence. Probably both of those things don't help you at this point, but keep it in mind. Still wiht an Y / X field pair sort you should be able to accomplish something like the Upper Right, Upper Left, Lower Right, and Upper Left sorts. Reversing the X and Y order would give priority to east/west movement over north/south movement.
I have not seen the results of the ArcGIS 10 tool myself, so I cannot be sure they don't have a fancier algorithm under the hood. They also have a APEANO option that I do not fully understand.
Anyway, with a set of X / Y fields you could previsualize the sort in a tableview and walk through the features to see if the order did what you wanted with any of the above sort orders.