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I've had a 3rd gen iPod nano since 2008 and it's still my favourite ipod to this day. I recently charged it up and the battery life is still excellent, but it's lacking in storage space so I don't use it that much. I'd still pick it if I could only have one though.
 
Very difficult question!

Of all the iPods I had, the only one I still use is the 2008 nano. It feels just right in the hand, 16 Gb is enough for me and you can make short movies, which I prefer over photos. I used the 2010 nano a while as a watch, which worked fairly well but I found out the hard way that wearing it in a rain-shower can kill it. And it showed a lot of signs of wear after 6 months. The 2005 shuffle was the iPod I used the most by far. At that time I travelled a lot for my work and I always slept in the plane with my trusty shuffle. But not having a screen was frustrating.

So 2008 nano: the perfect mix!
 
Probably my loyal 16GB iPod Nano 5. It has a great battery life, hasn't broken after dropping it lots of times, has a camera, a speaker, and you gotta love the click wheel!
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Only iPod Touches have been worth having for me. Latest is great (and has kept me from buying an iPhone).
 
I'd like an original 1G iPod (with moving scrollwheel), but SSD hard drive - bigger the better, but at least 250gb, touch colour screen as well as working scrollwheel and buttons, lighter battery, USB 3.0 interface and lightning port...
 
Another vote for the 5th gen. I love it's capacity and that I can use it with the photo connector to backup photos taken while on Vacation.

I am seriously looking to replace the hd and battery but I have irregular black lines across the screen so wonder if it is worth upgrading.
 
Personally, I've been leaning toward what I call my "Hipster iPod": an iPod Mini (mine is 1st gen blue) with a generous flash upgrade and a high-capacity battery. Classic design, modern storage.
 
I stand corrected. RetroSonic Fidelity sold iPod Mini's modded to 128gb (https://retrosonicfidelity.com/shop/retromod-mini-audiophile/retromod-mini-128gb-green-audiophile/), so 128gb must be possible.

After a bit more reading on the RetroSonic site (https://retrosonicfidelity.com/verge-256gb-retromod-minis/), I see that a 256GB iPod Mini is theoretically possible. Practicality of such a mod, though, is going to depend on encoding scheme since, as one commenter points out, the Mini seems to max at around 12,000 songs.
 
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