iTunes will probably be the toughest. I lean on iTunes for syncing files, media, local backups and if I had to ditch Windows tomorrow and decided Linux, I would set up iTunes in a Windows VM since I don’t think there’s any other workaround currently.

Reminds me of Technology Connections:

“I like to do work on my computer. Not work on my computer. And that’s why I don’t use Linux! Yea, I went there!”

Semi-related but I remember the ancient days when the original iPod touch (not iPhone though) initially had paid OS upgrades - not too crazy for back then when the firmware was often done when the device shipped save for maybe a small patch or three. But there were also larger updates too but not too common.

And then I remember Steve getting up on stage proclaiming that Apple “has found a way!” to make it free.

That’s incredible, happy to see the old hardware still kicking!

On a similar note, sometime a year ago I spotted a guy using a Q10 at a shopping center in LA. Had a quick chat which was fun.

Not an exact answer but I use Photosync to upload to my PC when on a shared network. It supports a number of protocols so I would see if it can connect to your server.