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Having used iTunes for a long time, my iPod Classic finally started showing signs of dying. I bought a FiiO X5II and put all my music onto it's microSD XC card(s) using rsync to ensure the same folder structure, using this command from my Linux Mint laptop:

rsync --ignore-existing --progress --recursive --perms --times --size-only --whole-file --exclude='.*' /Users/my-username/Music/ /Volumes/X5II\ TF2/Music

Likewise, I ran this same command again to rsync my music to my Linux laptop, as I figured that if I need to manipulate folder structures of my music, I'd prefer to do so where I have access to any open source tools to do anything I need, and not shoot myself in the foot by breaking all my playlists available on my MacBook.

Unfortunately, I didn't know that the FiiO X5II would have limits on how it can parse M3U playlists. The two issues I'm having are as follows:

  1. The FiiO X5II has limits on how long paths can be for locating songs listed in a M3U playlist. Within the 80+ gigabytes of music in my library, many of my songs have UTF-8 characters in their filenames, possibly causing problems with finding the files properly. This causes a problem for using M3U playlists when I'm limited to a file path character limit.
  2. I cannot seem to find the means to consolidate the files while keeping them organized. Either I can have playlists, or I can have accessible files.

That all stated, my question is if there's any way to manipulate the folder structure so that, from their original structure iTunes used (iTunes Media/Music/<Artist-Names>/<Album-Name>/<FileName>.<Extension>) to a structure that removes the Artist folders, pushing the Album folders up a level, recursively, so that it'll be in the format iTunes Media/Music/<Album-Name>/<FileName>.<Extension>.

The last question I have is a little more technical, but any info is greatly appreciated: Do the FiiO X series DAPs have a specific codepage they display text in? One issue I've noticed in running playlists on my X5II is that when attempting to load a file from a playlist that the player for some reason can't load, it will render some of the characters as boxes, making me think UTF-8 is not the default encoding for file names within the device. The only other explanation I can come up with for playlists not completely working is that the paths have to have spaces escaped. If anyone knows anything about whether this could be related to the previous issue, or if it does affect anything regarding files with UTF-8 tags/file paths, I'd REALLY appreciate it.

I have multiple backups of all my music files to take suggestions towards how to go about this, so any suggestions are welcome. :)

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Never mind: I've found the solution. An app called M3Unify is able to produce playlists and also export the music within the exported playlists. What makes this app different is that it can also rename the files it exports using tag substitution patterns, and can export the files as subfolders, with specific instructions detailing how the files are put in folders when exported. See below:

M3Unify-screenshot

Unfortunately, this solution makes it a Mac OS X-only fix, and not a UNIX/Linux-based solution. If there's any ideas that doesn't involve proprietary software, those suggestions are still welcome, for others to hopefully have use of. :)

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