The key to me, though, is the seamless integration between iTunes and the iPod, especially where metadata is concerned and its usefulness in smart playlists. For example, my 4Gb Nano 1G is automatically synced as follows:
Approximately 800 MB is reserved for data transfer and podcasts.
Any music added to the library within the last 60 days, having been played fewer than 5 times and skipped fewer than twice.
Approximately 70% of the remaining space is given to songs rated 4 or 5 stars and least recently listened to, 20% songs rated 3 stars and least recently listened to, and 10% unrated or 2 stars least recently listened to. (If I never want to hear a song again, I simply rate it 1 star)
The ability to rate songs on the fly from the iPod and have that automatically transferred is essential to this system, obviously, although I had a limited version of it set up for when I was using a Shuffle.

I can confirm that the new Nano will accomodate voice recorders. Personally, I just use my Treo on the vanishingly rare occasions I need to record a voice-note for some reason.

1. Unles you get all your music from the Itunes store, ITunes is shite. Go with MediaMonkey. It is free and has way more functionality than ITunes and ease of use than WinAmp. Any portable device works with it. All the tricks of ITunes and dozens more. I particularly like the auto-organize and auto-tag from Amazon functions.

2. Spring for the 8G Nano. Seems like having the space is well worth it. And with the exception of Microsoft’s new Zune, no other player out is quite as sleek and sexy.

3. Subscribe to eMusic. Based on your plan, you download a pre-set number of songs per month, all in mp3 format, with no DRM. Tons better than ITunes and roughly .25 per to Apple’s .99 per.

This is what I have, and I absolutely adore it: http://www.amazon.com/Creative-Zen-Vision-Video-Player/dp/B000CS7U1C/sr=1-1/qid=1158254768/ref=pd_bbs_1/103-0586464-2548606?ie=UTF8&s=electronics

My sister has a nano, so I played with hers a lot before I made my decision. Even she told me not to go with one.

I have used iTunes and I found it more of a hassle than it was worth. To me the simplicity of just moving files over like I would in Windows explorer (and more importantly being able to move files in BOTH directions) was much better.

I still don’t like them, mainly for DRM reasons. And I actually don’t agree with Skwid, I think the music management features of iTunes are restrictive and frustrating. I don’t know if you’ve use it much, but since it is free I would use it a while and try to “Manage” your existing music with it before you spend money on a device that will force you to use it.

Personally, I think the design and usability of the iPod family is fantastic.