I always water just before it rains. That way the new moisture pushes my watering fluids into the ground. :rolleyes:
Actually, since I cannot read clouds, I simply water when the ground is dry and it's not raining. In fact, those of us who live where the soil and air both tend to be dry may find that watering when it's overcast and darkening toward dusk uses moisture efficiently because it has a long time to soak in before the surface of the soil is baked by the sun.
In any case, it's getting cool here, and I will be spraying my roses with Freeze-Pruf once a month through April so that roses that don't drop their leaves have a chance at getting in a little root growth over the winter. No ski slopes here. Maybe no snow till January. Maybe some daytime highs in the sixties through much of the winter...