Sakamichi no Apollon 1-End
I just read all fifty chapters in two days... I can't remember who suggested this one to me, but just wow. That was exactly what I was looking for. It was one hell of a read too. I really loved that it was a period piece set in 1960's Japan. It was really interesting seeing the ways of the time. I also liked how all of the characters were flawed, and even when things are going right, those flaws are still present. That said, it's crazy thinking of where the story started and where it ended. That sure was one heck of a journey. I absolutely be re-reading it soon.
If anyone knows of any series similar in nature to this one, I'd love to hear it. This was exactly what I was searching for.