Rockbox Ports are now being developed for various digital audio players!
Check out "Disk Cache" in the manual. Turn it on, be patient the first time you reboot afterward, and hopefully your problems will be solved from there on out.
If I am not mistaken turning on directory cache TAKES AWAY RAM.... ?
What kind of files do you play?
Try checking the disk for errors, using chkdsk or equivalent.
Can provide a link to a failing file?
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