I live in Israel. Out here, "going nomad" as you call it (I called it "adventuring") is a traditional post-army experience, probably half of all Israelis will do it. Popular destinations include South America, Central America, and Southeast Asia. Basically anywhere that isn't yet too expensive, as a recently soldier hasn't saved up much money at all!
My trip was relatively short, almost 6 months. My backpack was larger, but then again, I had a sleeping bag, mat, tent, and water for when the adventuring when off-road.
I would've left the Zen at home. Think about when you're listening to it: On the bus/plane? You could be chatting with locals. When you're bored? Go out and seek adventure. Winding down before bed? If you're not exhausted by the time you hit the sack, you didn't try hard enough! But the most important reason is because you can buy a tiny, cheapo radio and listen to what the locals listen. I think that traveling should include absorbing some culture, too. Get a book written by a local author translated to English (or not).
Safe travels,
Eyal