Filling an iPod Nano

GREG: Now, my iPod Nano is 4GB, so it can't fit my whole iTunes library like my regular iPod. I'll need a strategy for which stuff makes the cut.
GREG: Clearly, a dynamic playlist makes sense, but do I order the songs by most recently added or most often played?
GREG: And there's the issue of podcasts. Obviously I want my favorites on there, but their large filesizes pose a problem.
BRETT: Hey, don't you need to get to work?
GREG: Took the week off. NOW... I've drawn up several endgame scenarios....