I'm torn between the 160 GB Classic, the original mini, and the 5G nano.
The original mini, for it's time, was just perfect. Perfect size, and gorgeous. Awesome feel in your hand, large clickwheel for in-your-back-pocket-navigation. It was my first iPod, and I used it for 3 years before I lost it. 1.5 years ago, I found a NIB one on ebay (silver 4 GB second gen, close enough as mine was a silver 4 GB first gen) so I bought it for $80. I pull it out when I feel nostalgic, like I did this past weekend. I used it all weekend and remembered what a great iPod it was.
The 5G nano, is just awesome and is just a 32 GB flash chip away from true perfection. I really don't care for the other features (video camera, radio, video, etc.) but it's an amazing little package, and has an awesome form factor that's hard to beat. It's so much in such a small, elegant package. I actually bought three of them--red, green, and orange, all 16 GB models. my only fear is that I have 12 GB of music now, so they are getting full but these are iPods I see myself using for several years, like my original mini so I'm concerned about them getting full.
Then there's the 160 GB 2009/2010 classic. I gotta admit, THIS is my go-to iPod. This is my favorite, it feels so good in the hand, I love the slab-sided size of it, especially in it's Switcheasy hard plastic case, and it's nice and fast, as mentioned the transfer speeds are insane compared to any other iPod, and it just looks beautiful. I remember when they came out I thought they were absolutely hideous (well, the black one still looks a little cheap to me, but silver, which I have I think is gorgeous), and I hated the split screen software, but now I love it. Even though I only have 12 GB of music, the Classic really is the best iPod for me, and my favorite. The battery is awesome too.
So I guess it's another vote for the newest Classic.
