If you want to get into more woodcock, find aspen clearcuts 5-7 years old. 3/4" - 1-1/2" diameter and thicker than the hair on a dogs back. This past weekend was our annual hunt with my brothers. Saturday morning we shot our 6 man limit of woodcock hunting two spots before lunch. It's tough going, but so much fun to get into flights of timberdoodles. And excellent work for a young pointing dog because they normally hold very tight.
We shot grouse, too. As you said, they're humbling. Fast and never seem to get up where you expect them to.
Grouse run, much like pheasants do. They'll run ahead into a clump of fir, then go out the other side, using the fir as escape cover. That's something to keep in mind when going in on your pup on point. Note wind direction and take a circular path around and ahead to cut the bird off when he goes. They're wily birds.
Better yet, is hunting with a partner and if you know how to hunt together it helps. Grouse will flush wild at the sound of human voice, so hand signals. One guy circling wide around each side of dog and expect the bird to be 20-30 yards ahead into the wind.
I had a buddy I took hunting a few times, but with too many reasons not to explain here, including safety, I no longer hunt with him. He just didn't get it. My dog would slam into point, he'd walk up and stand next to her. I'd be going around one side and the bird would go out the other, with him never being in position, despite my talking strategy over and over with him. One of my brothers refers to him as "that greenhorn son of a bitch", as he and I had a bad experience with him.
Over the years, my setters have often given me a clue as to range to the bird. Close to the point and they'll be crouched low forward, especially on woodcock. Standing tall and the bird is out ahead.