I started down this path after discovering that iTunes was flagging some of my music that I ripped from my own CDs or my dad’s old records (that I now own). It shows on the iPod as “not available in this region” despite purchasing the physical CD from the record store across town!
The iPod is used 99% of the time in my car hooked to the radio, but I’ll bring it into the office from time to time. I’ve been thinking to build something with a raspberry pi and big SD or SSD so that it shows up on my home WiFi when I park and I can syncthing or drag and drop music, but I don’t have a lot of time to play. The iPod was a Xmas gift from my dad and (I know it’s stupid) but I want to keep using it if I can.