I use my iPod Classic to this day. Main reason is convenience. It's very easy to switch songs on this device my feel when driving and through the click sounds.
But the main reason I use it is because I picked up some parts from China and the US to upgrade the drive inside of mine to use a RAID-0 array of micro SD cards to give me storage up to 1.6TB. Put in a larger back, and a 3000mAh battery you can easily find on eBay, and then I got a new mainboard for 2.0.5 to upgrade my 1.0 mainboard, and I now have a player where you can hit play for audio and come back to it in 14 days and it still has power left over. That thing is incredibly battery efficient. The reason it doesn't last long normally is because the hard drive sucks down a lot of power. Replace it with micro SD cards and an iFlash.xyz board and it's extremely battery efficient. No issues when playing back video, hires, audio... nothing.
One thing the iPod Classic does is smart playlists. If you set up the playlists right, it will recalculate them on the fly. No other player I've used can do this. I discovered this on a long road trip where I had a Not Recently Played playlist and noticed that the count decreased as I was driving when I'd jump out and jump back in. So with my extended battery life, I can charge this and synchronize it once a month and I'm fine.
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I have a 5th gen running 2 256gb sd cards for a total of 512gb. I also have a stack of other 5th gens I'm waiting on to mod. My next ipod I will probably do a 1tb, a 512gb ssd.
Watch out when you go over 1TB though. On mine, it won't format the drive if it's over 1TB in size.
To get around this, you have to restore the iPod in iTunes and wait for it to throw an error (which it would do at 50% of the progress bar). Unplug the iPod and it will say, "Connect To Power." (this is because they want you to be on power for the firmware install..... Instead of connecting it to power, boot into disk mode and format the drive from your PC as 16kB clusters (or however the disk format works in a Mac -- I've only tried this on a PC). When that format is done, unplug it from the PC and reset it. Connect it to power and then it will finish the firmware install on the formatted drive. The unit will now report all storage free.
And I had to do this when I first got 1.2TB and now that I'm up to 1.6TB. Just keep this post in mind in case you break the 1TB barrier because I first thought it wouldn't accept it until I played with it a bit and figured it out. You can definitely go over 1TB..... I think the limit on a PC is 2TB because of the FAT32 partition limit at 16kB/sector. I guess a Mac formatted iPod can go further.
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There are services that will still do it by mail. Not exactly cheap, maybe more than double what the parts (battery, memory, adaptor) would cost. but more peace of mind for me than risking breaking stuff. I used rapidrepair last July. Got a 192GB SSD with a new battery with no fuss and works great. Note I went for 192GB and not higher because there is a max song limit on the Apple IPod OS. If you want more, gotta install Rockbox, which means no iTunes sync.
Rapid Repair is expensive but I hear they are good. I used to buy an SSD until I discovered iFlash.xyz
You can get an iFlash Quad and use up to 4 micro SD cards. It will take up to 400GB cards just fine. I haven't tried the 512GB cards yet since they're not readily available, but if I get one, I'll definitely give it a try.
But most importantly on the upgrade..... if you don't have an iPod 5th generation (5.5 too) or a 7th generation, do not go over 128GB. So if your iPod classic (6th generation) is not running firmware 2.0.4 or 2.0.5, going over 128GB will yield you nothing unless you use Rockbox. The system can't address it. You can get a 2.0.4 or 2.0.5 mainboard on eBay easily enough and you can just swap them out.... but keep that in mind if you try it.
The iPod Classic is not hard to open. You pretty much have to pry it open on the edges and once you get it open, it just comes off. Nothing too involved..... but it can bend the base plate if you do it badly enough... but you can bend it back or just get a new plate. Just be careful when you take it apart not to pry apart where the screen is or near the ribbon cable on the left side (when looking it from the bottom).
Lauren
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I still have my 7th gen 2009 160 GB, still works great, still holds a charge, still looks brand new.
I retired it as my primary player when I got AirPods and begrudgingly moved to usung my phone, but my classic still gets played daily in my car.
These iPods seem to sync so much better with iTunes than iOS devices, NEVER a problem syncing this device.
Apple still offers $299 out of warranty service fees and $149 battery service on these. Wish I knew how many cycles were on the battery.
You can buy a 3000mAh battery with a large backing to the unit for about $20 on eBay.
Considering your stock battery is probably 650mAh, this gives you at least 4x playback time..... for $20.