Lost settings when rebooting iPod from Rockbox back to Apple firmware

I am a recent convert to Rockbox, and I love using, exploring, and customizing it.  But there are times when I need to (or want to) use the original Apple firmware, such as for playing the ~250 songs I purchased from the iTunes Music Store in the early/mid 2000s and that still have the DRM that prevents them from being playable by Rockbox.

The problem I'm having is that when I reboot the iPod with the hold switch engaged in order to use the Apple firmware instead of Rockbox, the user settings that I had previously set when previously running the Apple firmware all get reset to factory settings.  This appears to be an Apple 'feature' for booting with the hold switch engaged.  Is there a way I can reboot into the Apple firmware without having those settings reset?  I have tried searching both the Rockbox website as well as the web at large and have not found a solution (or even a mention).  Thanks in advance to anyone who might be able to provide some insight into this.

PS - I thought there used to be a way to purchase upgrades for the DRM versions of iTunes Music Store purchases but I haven't been able to find out anything about that, too.  Does anyone here know anything about that?  Thanks again.