First of all, I'm glad you are aware that you can't keep both. The reason Boots "used to be nothing but a rapist who didn't care about his hens" is, Boots is still a cockerel. An immature rooster, operating solely on hormones. Since he is still young, there is a good chance you can start now to train him to respect your space. When I have cockerels, as soon as I recognize their gender I start "training" them. I distance myself from them. I don't handle or hand feed them. When they're old enough to be outside, I will "walk through them". If they are between where I am and where I want to be, I don't go around them. I make them move out of my way. If one challenges me, I meet him with confidence and make him back down.
While I agree that "some" roosters can be friendly, I believe there is a HUGE difference between friendly and not human aggressive. I prefer the not human aggressive ones. If you do some research on the site, you will see that many hand-raised, hand-fed, babied "roosters" (usually more often cockerels - roosters under a year of age) will turn on their keepers. They are hormonal, intact male animals whose instinct is to breed and protect their females. Sometimes those instincts will prompt them to lose their minds and attack the giants who take care of them and bring their food. When that happens, they're not doing their "real" job of protecting and caring for the flock.
I think you've made the right decision in getting rid of Milo. It's bad enough that he attacks you, but worse that he attacks your friends. That is a liability. If he were to hurt one of your friends, or they were to get an infection from a puncture wound or scratch, you could be financially responsible for medical bills.
