To try to respond in order so I don't forget anything:
All of our hens have names, because they all have their own personalities. I do get some of the same colored ones mixed up, as two of the lavender orpingtons look very alike (Violet and Peony) and three of the chocolate orpingtons grew to look more alike (Theo, Cookie and Biscuit). Calling them by their names isn't weird to me.
Mature hens may take longer to accept a young rooster, especially if they feel he has poor manners. It sounds like they are starting to accept Princess, which is great. For Mr. Roo they may need more time. Hopefully they will stop running him off so he can get some food and water and the safety of the coop at night.
Mr. Roo's behavior toward you: he could be aggressive, or he could be courting you. I can't tell from your description, it could be either. My friend's rooster Elvis used to stalk me across the yard and go for my legs with his spurs. My parents had a rooster, Fred, that would escape the coop and look in house windows until he found me, crow until I came outside, then walk next to me, offering me little bits of this and that, chirring, trying to lead me back to the coop where I belonged with him. The difference is body language. I don't have good advice on how to gentle Mr. Roo if he's being aggressive. I have a low tolerance for aggressive roosters, as I still carry a scar from Elvis. If you are looking to gentle Mr. Roo, I'd suggest making a post about options.
As to Cat and her Kittens: I see you have a Trojan Kitty (a friendly cat that was hiding more cats). If it were me, I'd start looking for some help. A lot of the US and Canada has cat rescues that are happy to help in that situation. They will come out and live trap Cat and her Littles. Cat will be spayed, as will her kittens, helping to stop the cycle of feral cats (which is great for cat quality of life and local wildlife). Outside kittens get sick easily, so its safer for them. Feral kittens are easier to domesticate while young. Most rescues will place the little family in a foster home until the kittens are weaned, then mom and babies will be adopted out. You won't have to worry about looking for cats outside before letting Toby out, and the cats will all go to homes. I'd do an internet search for local cat rescues and make some calls.