Has anyone had any luck with propagating oaks from cuttings?

It is not difficult to propagate from cuttings but you use small cuttings not branches. The diameter of your cutting should be no larger than your little finger. Pencil size is good. Your cutting should be 6" to 8" long. No leaves. Make a straight cut just above a leaf node for the top of the cutting and an angled cut just below a leaf node for the bottom. I start cuttings in 3/4 - 1 gallon nursery pots filled with all purpose potting soil within 1" of the top. 1/2 of the cutting should be in the soil. Use root hormone if you like but it is not necessary. Start several cuttings. Keep the soil evenly moist at all times but not soggy. That means daily watering and in the heat maybe twice daily. It takes about 2 months to root. When the cutting starts pushing foliage it is rooted. When leaves appear the cutting needs sun. Keep your starts in a container for 3 to 5 years before planting in the ground. Keep potting up to a larger pot. Your final pot size should be 3 to 5 gallon.

Go to a garden center and getting rooting GEL. For woody plants this is much more successful. Also while there talk to plant people to get tips and hints on how to do it the best.