Thanks for the suggestion, I think you had mentioned that on here a while back.
I've always preferred to be in control of my tagging and transfers, opting to do it manually, but since getting a second 1TB card I find I can lose track of what I might have quickly added to one, forgetting the other.
What I find what works is creating a master repository of all formats of my music. On a disk called Masters I have the following folders, AIFF Master, DSD Master and FLAC Master. In AIFF Master and DSD Master I store the master copy of the music in its native format with all required tags and art work. I also add the resolution for High-Res content in the folder name for the albums (examples are show below). From those masters I create a FLAC master and store in the FLAC Master folder. If the master is a 24/192 or DSD I also create 24/96 and 24/88.2 copies respectively for playback in the car. By creating the FLAC copies from the masters I'm assured that the tags are correct.
I created a naming convention for keeping albums in chronological order to get around the problem if there are multiple releases in the same year.
101 - 199 Studio
201 - 299 Compilations
301 - 399 Live
401 - 499 Soundtrack
501 - 599 Ambient
Here is a partial tree listing showing how I organize my folders (this is for FLAC for DAP, but same structure for all formats):
|____A
| |____a-ha
| | |____101 - Hunting High and Low [Hi-Res] — 192kHz · 24bit
| | | |____01 Take On Me.flac
| | | |____02 Train of Thought.flac
| | | |____03 Hunting High and Low.flac
| | | |____04 The Blue Sky.flac
| | | |____05 Living a Boy's Adventure Tale.flac
| | | |____06 The Sun Always Shines on T.V..flac
| | | |____07 And You Tell Me.flac
| | | |____08 Love Is Reason.flac
| | | |____09 I Dream Myself Alive.flac
| | | |____10 Here I Stand and Face the Rain.flac
| |____AC-DC
| | |____101 - High Voltage [Hi-Res] — 96kHz · 24bit
| | | |____01 It's a Long Way to the Top (If You Wanna Rock 'n' Roll).flac
| | | |____02 Rock 'n' Roll Singer.flac
| | | |____03 The Jack.flac
| | | |____04 Live Wire.flac
| | | |____05 T.N.T..flac
| | | |____06 Can I Sit Next to You Girl.flac
| | | |____07 Little Lover.flac
| | | |____08 She's Got Balls.flac
| | | |____09 High Voltage.flac
| | |____201 - Who Made Who
| | | |____01 Who Made Who.flac
|____B
| |____Band, The
| | |____101 - Music from Big Pink [SACD] — 2.8MHz · 1bit
| | | |____01 Tears of Rage.dsf
| | | |____02 To Kingdom Come.dsf
| | | |____03 In a Station.dsf
| | | |____04 Caledonia Mission.dsf
| | | |____05 The Weight.dsf
| | | |____06 We Can Talk.dsf
| | | |____07 Long Black Veil.dsf
| | | |____08 Chest Fever.dsf
| | | |____09 Lonesome Suzie.dsf
| | | |____10 This Wheel's on Fire.dsf
| | | |____11 I Shall Be Released.dsf
Once I have the appropriate masters I create folders for the respective use using the folder structure seen above on the appropriate disk, Library and Extra. Library contains the music for playback on my computer using Audirvāna Origin (AIFF and DSD). Extra has the folders Car and Sony that contains the appropriate versions of the music for that playback device. The Car folder only contains 16/44.1, 24/96 or 24/88.1 FLAC files to save space. The Sony folder has 2 sub-folders, WALKMAN and SD-CARD for the content that is stored in either the internal memory or microSDXC card. In those folders I'll have either the FLAC or DSD copies of the albums. I also place all of my playlists for the Sony in a folder called Playlists for the appropriate medium. This is to make it easier to keep track of the playlist for updating as albums are added, removed or resolution changes. I also make 2 backup copies of all 3 disks monthly and store in a fire proof safe.
One of the great things in macOS is that it's based on BSD and it includes or you can find ports of all the open source tools. So in macOS terminal I can run the following standard commands to list files by modification date in the current directory to see what was changed with newest first:
find . -type f -print0 | xargs -0 stat -f "%m%t%Sm %N" /tmp/* | sort -rn | cut -f2- | less
If you use Windows I can't help on finding what changed. Maybe someone else can help with that.
Once it's time to copy the files to the internal memory or microSDXC card I can use macOS Finder, Carbon Copy Cloner or rsync depending on how much I need to copy. If there is a large number or size of files for the microSDXC card I'll use a USB 3 microSDXC card reader which is faster than using the player USB 2 connection.
This organization journey started over 5 years ago and had many variations before I ended up with this methodology.