I've decided there isn't a simple way to do this. It all has to do with the original data. If each word was in a separate field, I could make this work and there is a way I could do that, but at some point, time spent building the script ends up taking more time than dealing with this manually. The data creator is also doing me no favors by having little consistency in naming conventions and properly filling in all of the data.
UPDATE: I've decided just to take over maintenance of this layer. I have a good enough handle on the data, I can maintain the layer the way I want to. The county will still handle my parcels and their data is still authoritative so I can still refer to it as needed. Thanks Dan for trying to help, your ideas would work in most situations.
Josh White, AICP
Principal Planner
City of Arkansas City