Exactly. The Crawleys care about their son's happiness and well being. They saw how tough it was on Fletcher to accept who he was and how it was made harder by being in love with August. They saw the effect it had on Lorraine's brother, and Roland's best friend, so understood it was a inner fight that couldn't be won. I think they are incredibly relieved that Fletcher and August came together.
Is Albert proud of August? I don't think you're wrong to consider it. He's starting to see himself in August, that try that he has, and yes, that double eagle might just be more than a coin. As you say, it says something. Still, the man is pretty much a monster, and August is fortunate to get away from him. I have to wonder if his gran knew this was the only way she could get(rescue) August away from his brute of a father.
Lorraine is being a mother, but she's also a smart woman. She knows what is needed to start a new life. They will be thanking her for sure.
Yeah, you've got the right read on Willy James. I'm sure they all worry for him for good reason. He's a townie, inexperienced about living and traveling by himself. Fingers crossed he gets away from his situation.
Thanks, buddy, for all your support.