@Omoshai. Welcome to Head-Fi. What you're going to find is that everyone here pretty much listens to music in a unique way compared to others. I think that I have a good understanding of your challenges ahead.
I have to apologize for the length of this post. For most this will be TLDR
First, to answer your question about no file. I believe the issue is that playlists are like a table of contents and the music file is your content or chapter. The playlist is trying to direct the player to the location of your file. So you need to make sure that the playlist is pointing to the correct directory location of your file, and that the file has actually been copied there. The Apple Eco system does a great job of creating your playlists, and then copying your files over for you and you just play.
To do the same thing in an audiophile DAP, you have to carefully create your directory structure, have your playlists in the correct directory location for the DAP to read, have the Playlist files formatted correctly to point where your music files are, have the music directories formatted correctly to where the playlist is pointing, and have the file named correctly and in the correct location. (Anyone who uses playlists feel free to correct anything that I've said incorrectly.)
Unfortunately, I can't help you any farther than this. As I don't use playlists on my audiophile DAPs. Here is the unique way that I listen to MY music.
1. 320CBR MP3>Normalized to 90dB with MP3 Gain program>Itunes 10.x>Smart Playlist>Ipod Nano 16G>LOD>RaySamuels Intruder amp>Trinity Audio Delta VII iem with gunmetal filters>Trinity Kombi tips>my ears.
2. FLAC Files>MicroSD card>iBasso DX50>multiple different amps>multiple different headphones and iem.
Also. I'm on Windows platform, so some of the programs I have may not be usable on MAC.
1. Apple Hostage situation.
As you can see, I am held hostage by my use of playlists and Apple. Through the years, I have rated each and every one of my 35,000+ songs from 1 to 5 stars. I create smart playlists that select my favorite music and ensure that I haven't heard it in a long time. For example, for the Nano, I will create a 200 song playlist. I will have iTunes randomly choose 75 5star songs that I haven't heard in 3 months or more, 75 4star songs that I haven't heard in 6 months or more, and 50 3star songs that I haven't heard in a year or more. As I listen to the songs, the date/time played will update, and it will fall off the playlist and new ones will be added. I love hearing my favorite songs this way and never know what is coming up next. Also all my MP3s are normalized with "MP3 Gain" program at 90dB so that I don't get extreme changes in volume by switching between the different songs.
Unfortunately Apple is driving me farther and farther away. I use an ipod Nano 6G with the 30 pin dock. My itunes is frozen in time at 10.x. My aftermarket equipment is 30 pin docks. In fact, I just cracked the screen on my Nano 6G two week ago and had to venture onto ebay to get a replacement because I'm not willing to move to the Lightning system. I'm going to try to get another nano 6G or two and to fix the one I have. That way I should be covered for a while with my itunes listening equipiment.
2. Audiophile listening experience
The other way I listen is with FLAC lossless files. For ripping FLAC files (and also for ripping into iTunes), I use the program "dB Power Amp". I rip to FLAC level 5 and have it evaluated for "replay gain" and embed that information into the files. I pretty much just rip these to a FLAC directory structure that mirrors how iTunes is set up. I have a 2TB hard drive with :\\FLAC\Artists\Albums\01...file. Very similar to what Nick Matheis showed you above. After I rip in FLAC, I use the dB Power Amp function to convert those to MP3 320CBR and import those into iTunes. I essentially have a huge database of 35,000+ MP3s, and I'm slowly ripping my favorites to FLAC and anything new I purchase is ripped to FLAC.
For listening to my flac files, I hook my DAP up to one of my many different amps via line out. I have a Ray Samuels Intruder amp which has balanced output or single end output. I have a Peachtree Audio Decco 65 desktop amp with a coaxial input, and a Unison research SH class A tube amp with line input. I also have a few other portable amps but I mainly use one of the three above.
When I listen to the FLAC files, it is more like when I was a kid growing up and I will choose what album I want to listen to, and listen to the entire album all the way through. Also, the DAP I have at this time, (Ibasso DX50) does not currently have replay gain functionality. So any kind of random or playlist functionality would have large swings in volume. Which I hate. I'm excited to see that the N3 will have replay gain. I've embedded all my FLAC files with replaygain info, but have never gotten the chance to try to use it.
So as you can see, my audiophile listening is more geared to artistic album pursuits, and my casual listening is apple playlists.
I honestly don't know what I will have to do when the apple platform forces me off of the ancient 30 pin equipment. Guess I will have to leave apple behind at that point and change how I listen to music.
I don't know if this helps at all, but I do understand your challenges, and wish you the best with the way that YOU listen to your music. Let me know if you have any questions.
