So there's a loosely connected book series by Gary D. Schmidt

Each book can be read totally independent of the others, but they have some characters and a time period in common.

The Wednesday Wars won the award, but interestingly it's always Okay For Now that people search up at /r/whatsthatbook. ( Minor spoiler )

Anyway, there's a new one out, Just Like That. ( Bigger spoiler )

Worth a read, though I don't think the second protagonist's story holds up if you think about it. ( Read more... )