Hi Sean,
Sorry not to have replied sooner as I'm only now just back in Maine after a nice visit to Columbus, Ohio for my sister-in-law's wedding. In my test done earlier this morning for this issue using J-Field v1.10.3.17463, I saw no problem. I was using a 16GB USB stick.
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Please make sure that 1) you're deleting all old backups and that 2) the USB stick has ample room. Obvious stuff I realize, but had to mention it.
The specific file that failed to be backed up during your efforts, is it always the same? This is somewhat rhetorical as I cannot see but only the first bits of the full path of the offending file (sure would be handy to have word-wrap). But when I go combing through the stuff in my LS's:
Computer\Compact\Storage Card\VS Data\UpdateService, I found (5) sub-directories under which were more folders, but none of those folders actually displayed any files:
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So what? I dunno as these areas creep into the vastness of my ignorance. Misha could probably give us the best advice and whether or not deleting them could help resolve the problem that you're experiencing - I'd wait to hear from him first before trying that.