Can't play any music or update the database

[Psychotronics]

I'm running Rockbox on an iPod Video 6th gen using iFlash Dual.
I know the iPod can get finnicky on iFlash, so I'm trying to understand what is going on. It used to work just fine, but now it won't play any songs. All the folders show up, the files are there, but if I click on a song it'll just skip and go back to the menu. If I try to update the database, it goes on for a bit, shuts down and I need to do a hard reset to get it back on again.
I know I can get past this issue by formatting the drive and installing Rockbox all over again, but I'd like to get a better understanding of why this is happening to try and make adjustements: maybe buy a different memory card or something. Is there anything I can do on debugging mode to get more info on what's going on under the hood?