How the first gen ipod was reverse engineered to run #Rockbox:
1. Someone figured out that when loading a particular HTML page (for viewing on the device), the device would reboot. It crashed. A buffer overflow in the HTML viewer!
2. The device remembered what it did before the crash, so it would reload the HTML page again after boot. Unless you connected to it over USB and removed the HTML file it would stick in this cycle.
(continues...)
Maybe try a Windows VM with USB passtrough