Apple iPod and Apple MacBook Pro

Why can't I connect my iPod to my MacBook Pro? Both are legitimate devices, both are running legitimate software and my music is all purchased. I want to run my music from both devices (I don't want to run my MacBook in the garage) but for some unfathomable reason I can't any more.

I'm sure Windows devices don't have this ball and chain restriction on playing your own music.

Kindly explain your logic, Apple.