RE: unique management situation
Buck,
I hesitate to do an annual becaues if i have leave, the field will not get replanted, the annual will die and weeds will come in.
Having the field mowed will not be a problem. Even I am not there, in fact my concern would be it getting mowed to much.
I am not sure about your area, but in northern WV red clover/orchard grass is a very popular, successful hayfield mix. Cut twice per year, i belive that the clover can still flourish and If I leave the orchardgrass can take over and the field will be fine for what is used for now, nothing.