number 6 - the nano IS an iPod - just a different one from the iPod classic. Over the last few years, I've acquired 3 sizes of iPods (classic, nano, and shuffle) which I use for different purposes, and I've been very happy with them. I've run into the occasional glitch with the iPods or iTunes, but have always been able to resolve these after a bit of web research. From what I've heard, similar problems or worse can occur with any brand of players.

The one bit of advice I'd give is that you don't input any iTunes or iPod updates the moment they come out. Wait a few weeks, and check iLounge.com or the iTunes/iPod forums on the Apple website to see if any problems are caused by the updates. Often, there's a second update a few weeks later to fix these kind of problems. I'd then wait a few more weeks, and if no major issues surface online, then it's safe to update.