I picked up an iPod Nano as a birthday gift to myself, and love it. It’s small and light enough to fit in my shirt pocket, and I’m finding that even 2 Gig is enough for a wide range of my randomly-sampled music library (plus podcasts, which is really what I want to use it for).
The one big problem I have with it (besides still needing to buy some sort of sleeve to protect its screen) is what to do with the headphones when I’m not using it. The ones that come with it are always a tangled mess after sitting in my pocket, and the Javo Edge retractable kind seemed fine on my normal iPod but now actually takes up more room and is twice as thick as the iPod itself!
The problem of “what do you do with it when it’s not being used” is one that watches and belt-clip pagers have solved but iPods and cellphones headpieces really haven’t yet. Even wireless earpieces for cellphones don’t have a place when they’re not in use, though at least they don’t get tangled. It’s a harder industrial engineering problem than you might think, and one that I think often gets overlooked.