I would see how it goes. Sometimes a cockerel takes a fancy to particular hens and less to others and sometimes some cockerels are more gentle than others. The age can make a difference as can the length of their claws. I would stick with what you have and take it step by step. If you see that one hen is having a hard time, you could always separate within the run for a bit, keeping her with another.
Hiding places, and separate area of cover can make a huge difference. Alot less stressful for the hens.
Be mindful though. Watch your cockerel. Some are gentlemen and some are not. The ones that treat their ladies right, making sure they have their food, rounding them up a night, calling them together if there is danger etc are worth their weight in gold.

It is surprising though how many are just downright sods. Really nasty. Not worth keeping - for your sake and your hens. I have seen some attack the girls, not to breed but just being aggressive.