Just a couple of comments on iTunes and playlists. In iTunes (Win7) I open a playlist and click "File-->Library--> Export Playlist and save it (as a text file). This is a tab delimited format that can be pasted into or opened into a spreadsheet (I use Excel). Column AA (the 27th and last column) is "Location", which is the full path and filename of each playlist entry. I select the column and paste it into a text file with a m3u8 file extension, and then open the playlist text file in Notepad. I add the "#EXTM3U" hashtag to the first line of the file (replacing the "location" header tag that appears on line one the way I do the column copy from excel). Then I do a replace all, changing the d:\blahblah portion of the path that is not in the X1 with "tf1:\".
The X1 (and my X5 and I assume X3 etc) use "tf1" as the "drive letter" of the first or only sd card, and tf2 for the second slot of the X5.
There are different ways to skin this cat, using relative paths. But after fighting with that I decided to just hard code tf1 in the path. This has two benefits.... first, if I ever use a 2nd card on the X5 I can create playlists that span the two cards. Second, I can put my playlists in a dedicated folder on the root of the SD Card, which I prefer to do just to keep the root clean. By using the "tf1" drive letter I can put the playlists anywhere on the card and move them around if I decide to at a later time.
Here is a sample playlist...
#EXTM3U
tf1:\iTunes Music\Wes Montgomery\The Incredible Jazz Guitar\01 Airegin.m4a
tf1:\iTunes Music\Aisha Duo\Quiet Songs\17 Amanda.m4a
tf1:\iTunes Music\Billy Cobham\Nordic\06 As First I Saw You.m4a
In my case the "iTunes Music" folder is located on the root of my X1 (and X5) SD Card.
There has been much more discussion of playlists and file pathing in the main X5 thread. Do a thread search on "Playlist". Maybe the X3 thread(s) too, I didn't check.
I've also seen some comments that iTunes folders are poorly organized. Most of my stuff was ripped from CD using iTunes, although some are added to the iTunes repository using File-->Add Folder To Library when, for example, I rip something from Foobar and then convert to AAC (I don't store lossless in my iTunes library because of space concerns on my laptop and I just started building a lossless collection). I also have a fair collection of music downloaded from Amazon that is automatically imported into iTunes (and physically copied to the iTunes library). Anyway, all my music is organized by artist\album and AFAIK all my music has embedded album artwork. So for me, iTunes-->Fiio DAP has been very easy and seamless. The tweaking of the playlists is a PITA but I don't think there is any (hopefully free) software out there that could make it as painless as iTunes and an Apple device.
All the above would work equally well if you export a playlist from Foobar or some other app. You would just save the step of the temporary import into a spreadsheet.
I use a shareware program called BeyondCompare. It's mission is to compare, diff and sync folders. It is one of a handful of utilities that I can't live without on any Win machine I use. It's cheap and shows visually the differences in large folder structures. I use that to keep my DAP MicroSD card in sync with iTunes and some other folders of music I maintain outside of iTunes. It can also do a binary compare of two identical folder structures, and as such can be used to verify that everything on the MicroSD card is readable.
Anyone that has a poorly organized iTunes library might want to investigate the use of the File---> Library---> Organize Library... menu option. That should reorganize your iTunes library into an Artist/Album Title structure. If you do that, I would highly suggest making a good and verified backup first
. Just in case you don't like the result. There's no UnDo for that. In the preferences (Edit-->Preferences-->Advanced) there is also an option "Keep iTunes Media Folder Organized". I do NOT have this option checked, but my library imports are organized well. I think that option renames filenames and folder names in the event you make changes after import? It's probably a good option to use, I just don't like surprised so I never messed with it
I mention this stuff because I've seen a lot of comments strewn through this thread suggesting people are having problems I don't have. HTH