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I’ve been craving a truly retro-style MP3 player lately.

Still enamored with my old Surfans F20.
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Love the actual physical buttons, including Alps click wheel. Has dedicated analogue line out, though headphone out is good with efficient IEMs. I still love my old iPod 4th gen too, can't believe it's still working, but the headphone out is not as good.
 
Any reason or just a personal idiosyncrasy?
I prefer using a device that isn't my phone to listen to music, because my iPod doesn't pester me with notifications, calls, emails, social media, and so on and so forth. There are less distractions, and you can focus on the music more easily. I also believe in decentralization as a means to improve my experience with everything over all. I would way rather lug around a backpack with a good device for every task - a camera that is a good camera, a laptop to type on, and a gaming handheld - than one device that is mediocre at everything, like a phone that has a mediocre camera, a keyboard that will give you carpal tunnel syndrome faster than you can type the words "carpal tunnel syndrome" on it, terrible touchscreen controls that make for a horrible gaming experience, and awful locked-down software that steals your data and kills cute puppies or something like that.

Also, it reduces my dependence on my smartphone. Talk about putting all of your eggs into one basket. If you use your phone for everything, and your phone breaks for some reason, everything is gone. If you have a dedicated device for most tasks, your phone can break, and your sentimental photos of christmas 2012 are still on the SD card in your camera. Your songs are still on your iPod. Your savegames are still on your Nintendo whatever-it-is.

The longevity is improved too. My Canon DSLR from circa 2010 served my dad well, and now it serves me well. I have had no problems with it.
Same goes for my iPod from circa 2009. It served my dad well, and now it serves me well. I have had no problems with it.
Same goes for my Nintendo DS from whenever the Nintendo DS released. It served my dad well, and now it serves me well. I have had no problems with it.

I challenge you to find someone who still uses a phone from 2009. The old cell standards are unsupported, the software and operating systems don't get updates anymore, and so on and so forth.

Hope this helps.
 
I prefer using a device that isn't my phone to listen to music, because my iPod doesn't pester me with notifications, calls, emails, social media, and so on and so forth. There are less distractions, and you can focus on the music more easily. I also believe in decentralization as a means to improve my experience with everything over all. I would way rather lug around a backpack with a good device for every task - a camera that is a good camera, a laptop to type on, and a gaming handheld - than one device that is mediocre at everything, like a phone that has a mediocre camera, a keyboard that will give you carpal tunnel syndrome faster than you can type the words "carpal tunnel syndrome" on it, terrible touchscreen controls that make for a horrible gaming experience, and awful locked-down software that steals your data and kills cute puppies or something like that.

Also, it reduces my dependence on my smartphone. Talk about putting all of your eggs into one basket. If you use your phone for everything, and your phone breaks for some reason, everything is gone. If you have a dedicated device for most tasks, your phone can break, and your sentimental photos of christmas 2012 are still on the SD card in your camera. Your songs are still on your iPod. Your savegames are still on your Nintendo whatever-it-is.

The longevity is improved too. My Canon DSLR from circa 2010 served my dad well, and now it serves me well. I have had no problems with it.
Same goes for my iPod from circa 2009. It served my dad well, and now it serves me well. I have had no problems with it.
Same goes for my Nintendo DS from whenever the Nintendo DS released. It served my dad well, and now it serves me well. I have had no problems with it.

I challenge you to find someone who still uses a phone from 2009. The old cell standards are unsupported, the software and operating systems don't get updates anymore, and so on and so forth.

Hope this helps.
Interesting! Of course you are free to do things as best suits you, but some of your reasoning doesn't really make sense.

1. phone notifications distract: you can disable them. I have always allowed zero notifications on my phone. Not even for calls or texts.
2. decentralization as a means to improve your experience with everything rather than something that is mediocre at everything: phones are equally competent at playing music files as are standalone music players. (Or do you think this isn't the case for some reason?)
3. reduced dependence on smartphone, if phone breaks you lose your music: so you plan to put your music on your phone and a standalone player as a redundancy mesaure? Otherwise, if you just put it on your standalone player, the risk is the same--if the player breaks or you lose it, you lose your music. Anyway, the cloud makes this irrelevant. Dropbox + big hard drive back at home is a lot better redundancy than two small portable devices.
4. longevity is improved: It's true music players last a long time (I still have a functioning ipod touch from 2009), but if you own a phone and then buy a separate music player that is just more stuff (and more eventual waste). If you were suggesting a standalone music player without also having a phone, your reasoning would be sound, but I don't think you are.

Again, I'm not responding to convince you that your choice is wrong, just taking issue with the rationale. And of course you don't need any rationale at all for buying and carrying and using whatever devices you prefer :)
 
I too am struggling to find something that combines the iPod-like physical and software interface (minus iTunes), iPod battery life, good audio direct from the headphone jack (Apple dongle level).

iPod Classics still sell for $100-150 today, and parts are easily available (including batteries), so it would make sense to piggyback on this ecosystem somehow and fix the sound.
 
For more fun, you could get an older Rio Cd player that also supports mp3 cds. Doesn't hold much vs an iPod, but fun and can play cds gapless
 
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