Lemmy itself is still a work in progress and the new version apparently makes some major changes from the current version.
Sync is currently in a usable stable state so instead of squashing bugs in the current Sync version it was a better use of their dev time to work on a build for 0.19.
Unfortunately Apple seems to be actively working to make sure that the only way an iPod can be loaded with music is by using iTunes which is only supported on Mac or Windows.
You have a few of options on how to move forward:
1: Make a Windows virtual machine, install iTunes onto it and pass the iPod though to the VM.
2: Install Rockbox (if able) onto the device to enable it to act as a USB mass storage device allowing drag n drop loading of music.
3: Sell the iPod and get one of the many different digital audio players available on the market as most are OS agnostic (they show up as a USB mass storage device) and most use MicroSD cards to store the music meaning you can move the card to a new player as you upgrade later (so you are not locked to one vendor).
You can use the greater-than sign to make code blocks but for some reason it then picks up your use of pound sign as the formatting for headers even though putting text into a code block should stop that.
Are you sure he didn't leave because he couldn't find the exit?