I like to self host my stuff and have an Airsonic server with all my music. I can connect to it via web or a number of compatible apps available in the Play and App Stores. All the convenience of streaming and none of the subscription fees
this post was submitted on 08 Sep 2023
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If I wanted to do this today I would use iTunes and an old iPhone as the mp3 player. I would use an old laptop to rip, or iTunes to purchase.
In my experience it isn't if it'll work, it's if it'll have enough space for all my music. I still have a couple old iPods, including the original Touch, but I have way more than 16GB worth of music now.
If you just want something simple for your own music with no ads, check out iBroadcast.
I'm not certain, but you might be able to make an iPod Classic talk to an iPad (you might also be able to do it with a raspberry pi + Linux + iTunes running in wine). If it does work, there's the catch that you'd have to convert your files to aac (also known as m4a, lossy and similar to mp3) or alac (lossless and similar to flac).
If you try an iPod and rip CDs or convert from flac/wav, make sure you convert directly to your desired iPod-compatible format, avoid converting from mp3->aac unless you don't have the original lossless rip. Doing so is like repeatedly opening and saving a jpg. Each time you do it, you lose some quality.
I just put them on my phone. All you need is a USB cable (BT and wifi probably aren't going to cut it for a bunch of music files at one time), and somewhere to transfer the files from. I use Vanilla Music because that's what I'm used to, but VLC is available too.