The primary enclosure for our sheep is a 2-3 acre pasture at the northern end of the property. At the southern end (separated from the pasture by a few outbuildings and other areas) is a sizable grassy meadow, in which we have planted dozens of fruit trees. Those trees are not yet mature, and are still fairly short (i.e. with lots of branches right at sheep level). We've protected them as well as possible using chicken wire enclosures, but it's far from perfect. In other words, as wonderful as that area is for grazing, we can't turn the sheep loose in there without supervision. Perhaps in a few years the trees will be tall enough, but not now.
I don't mind supervising them; I've set up a plastic chair, and enjoy having a cup of coffee in the morning as I watch them graze. If they get too close to a tree, I walk over and shoo them away. But the kids and I have discovered something even more fun for the late afternoons: they help drive the sheep down from the pasture, and then we all put on baseball mitts and toss a tennis ball around as we supervise the flock. If the sheep get too close to a tree, one of us is usually close enough to drive them away. And then it's back to playing catch.
Until it's time to drive them back north, of course. I clap my hands three times and shout "Let's GO!" The sheep have learned that this is the signal, and they usually begin stampeding back across the property. The kids have great fun chasing the stragglers, and Scooter loves getting out in front of the flock and leading the way.
This is my idea of multitasking.