Inspired by @Shrigglepuss to try again, I picked up an Anbernic RG28XX to use as an mp3 player. (I installed Rockbox on it, like Shrig did with the RG Nano). I'm really enjoying it!

I'm enjoying this little pocket game device with Rockbox on it. It took a little bit to install Rockbox. If this model had WiFi like most of their new models it would have been easier, but for nerd stuff it wasn't too bad. The 28XX connects to my desktop via the included USB cable, and I can dump music on it. It's pretty small, a little bigger than the Gameboy Micro.

If you're familiar with Apple devices you'll notice that I don't have to do any of the cursed things that Apple requires to get music playing in my headphones. Indeed the act of listening to music is remarkably free of interference.

The 28XX has two microSD card slots. I can now take my live recordings and listen back to them on this, without doing anything on my computer or in clouds. It's so tremendous and worth it. The entire process of listening to music on my iPhone became so miserable.

I'm also really enjoying Super Street Fighter II Turbo Revival for the Gameboy Advance.

@slimes so beautiful with the purple! 
@slimes @Shrigglepuss great idea! i have an old ambernic RG280V. i hadn't thought of using it as an mp3 player but that's a great idea. it also has the the dual micro SD cards