I don't know if a translation note was needed for "hare otoko", could have just said "That man always did know how to brighten up your day, didn't he?"
and while of course I'm hoping for a romantic ending, I think it's important to note that his interactions with Madoka have been, while regular and enjoyable, only a small part of his life. He's always had family concerns behind the scenes, and his own job, and probably other hobbies and stuff as well. We all have friends who we hung out with, but then moved away, and that's the end of it. Part of your life until one day, they're not. And it's not a malicious thing, or even a tragic thing, it's just how life works. idk, maybe I'm projecting here, but that last page really had me in my feels...