I don't think that would really work for us, since we still want to show ownership that fits within the parcel. Otherwise, our table would be too large (we have 3670 parcels).
Is your platform SQL based? If so, then you should be able to easily do what you want in sql server. Stack Overflow has more than a few questions about iterative numbering. This link sequential - Sequentially number rows by keyed group in SQL? - Stack Overflow has some good ideas. After numbering your records (based upon the groups), convert back to a shapefile. Your labeling can be based off one of the new fields. You could include some extra code if you only want to label polygons that are less than a certain size.
I have thought about this, and it looks good, so I think I will try something along these lines.
I'll have to fudge it a bit, and just set a physical size limit to labelling, instead of relying on ArcMap to handle it for me.
This sounds like the fastest and least stressful way to do this, especially when our parcel map changes with splits and subdivisions.