I’m currently dual booting Linux Mint and Windows. Love Linux, hate Windows. So why I am dual booting?
Because I own and use a Microsoft Zune HD.
It’s probably the best product Microsoft ever came out with. It’s so much lighter than my phone, it has a ton of my music on there, and it has an HD FM radio tuner. However, the software that runs it has never been released so there aren’t really any good options to try and manage the Zune on Linux (some people have tried, it doesn’t really work). So I keep a windows partition just so I can manage a 16 year old mp3 player and radio. That has to be the worst reason to keep a Windows partition, right?
(The reality is I would probably get rid of the Windows partition if I could, I’ve tried but something seems wrong with the BIOS on my computer idk I’m not a programmer. The Zune software is pretty janky at the point so uploading new music barely works anyway).
Well I get why you stick to a hardware device you like… but honestly that’s 15 years old. You can get something better and cheaper delivered to your door tomorrow.
I personally went down a similar path while discovering https://www.rockbox.org/ was still a thing, looking for old iPod or Archos I could refurbish, checking 2nd hand market, etc. As much as it pains me to say, unless you are a collector it’s not “worth” it. You can get something ridiculously smaller, with more memory, more features, etc for the price of a meal.
IMHO it’s better to get rid of Windows by purchasing new hardware that is genuinely interroperable by supporting standards.
Ideally you’d check something like https://www.hanselman.com/blog/how-to-update-the-firmware-on-your-zune-without-microsoft-dammit but it might be more work than you want to put it. Maybe your local HackerSpace could help though.
My point finally is that freedom is quite important and feeling trapped daily is not worth ~$50.