She chases my lowest hen away from everything just for fun, she is just mean. So my cockerel (Sir Winston Churchill) is terrified of her! She chases him away from food (I have plenty of food in different places so that isn't the issue) and he hides from her. Will he stop being so scared of her and potentially keep her in line as he gets older?
This sounds like a hen that is afraid of losing her position in the pecking order so she is brutal to those that are still less dominant. One that does this is often one that is lower in the pecking order. She doesn't have much status and doesn't want to lose what little she has.
Eventually that pullet will mature enough to force her way into the pecking order, that typically occurs with mine within a month or so of them starting to lay. Laying tends to move them up a notch.
Eventually that cockerel will mature enough to become the flock master. Right now he doesn't have the self-confidence to do that. The earliest I've had one do that was five months, really rare. The latest I've seen was at 11 months. Most of mine can do that around seven months but that age can really vary. I think the personality of the hens has a lot to do with that age and how peaceful it is.
When I have a cockerel come of age in a flock of all mature hens (and pullets his age) Different things can happen. Several times it has been really peaceful. He just quietly takes over. There is remarkably little drama.
It's also not unusual for him to try to mate them and some or most run away when he tries to mate them. He often chases them and runs them down, grabs the back of their head, they squat, and they mate. Or sometimes the girls get away. I've never had a hen or pullet injured during this but it is by force so an injury is possible.
I've also had where some pullets or mature hens willingly mate with him, but the dominant hen is not OK with that. If she sees him trying to mate, even if the hen or pullet willingly squats, she knocks him off. He's not allowed to mate in her presence because she is the boss. I even had a dominant hen that would mate with the other hens just to show him she was boss. Eventually he matures enough to stand up to her and takes over. This is one of the very few times I saw serious fighting. It was pretty vicious for two days but she finally gave up and they became best buddies. In both these last two scenarios people I trust on here have said they have had serious injuries. I have probably been lucky but I also have over 3,000 square feet for them to use. I think that much space gives me an advantage.
I don't see any of this in what you describe because your brutal hen is not the dominant hen and she is also going after a pullet, not just the boy. I see a hen that is afraid of losing what little social status she has and is a bully to try to maintain what she can. I don't know how violent this really is or how much risk those two young ones are in. It will probably work itself out as those two mature but since violence is involved you need to keep an eye on it.
Or will he just maybe end up being a bit of a wussy rooster LOL?
That is a good question. Some roosters have more self-confidence and determination that others. A self-confident rooster can usually win over the hens based on his personality and magnificence. Usually, not always, because it's possible to get a hen that just won't submit to anybody. I believe a weak rooster that can't really win them over by his magnificence is more likely to resort to force. When he is still immature he may resort to force because the mature hens may not respect a snotty brat. But once he is mature a rooster that bullies the hens isn't much of a rooster, even if the eggs are fertilized.
2) we saw on our chicken coop cam that he crowed two nights in a row about a week ago, maybe 9-10 days ago? Anyway he did a real crow - loud and proud and scared himself half to death - but it was real crowing. Since then not a peep! Is it normal for a cockerel to stop crowing after he did it a few times?
I have no idea.