Seems a pretty good DAP to me.

Use roon with roon arc if you have a music server. You can sync the music losslessly to your dac, and have auto tagging and such at the hand. Its great!

Mine are sorted into alphabetical folders, then band name, then albums. The album are named after a standard (year first). The songs are named after another standard. All files have been either MP3Gained or Replaygained when I ripped them. Metadata is also standardized when ripping, so they have stuff like album art and other important information. Much of it is gathered automatically off the Internet of course, not hand-typed.

Then there are numerous ways of accessing them, in my personal case a Logitech Media Server (Squeezeserver/Squeezebox) that’s now open source does the honors. Been too cheap to go full Roon.

I must admit I don’t understand your pro and cons.

Assuming you mean DAP, it is a portable media player with an interface.

Most of the time this interface allows you to navigate your collection in various ways e.g. by Artist, Album, Composer, Genre, etc. You can make playlist as well.

So I don’t see why one has to listen to a whole album.

I mean… you can do both in both situations.

Listen to full albums or to playlists. Or just shuffle everything which is what I do on my DAP.

I use Media Monkey. I bought the lifetime version many years ago. No idea what it costs nowadays.

On the desktop, it does everything plus the kitchen sink, yet I’ve never really liked it that much.

The mobile (android version): terrible. I ended up sorting my playlists into folders (by dragging the folder off my desktop) then just selecting the folder to play the songs in media monkey on my phone. Also I have not yet figured out how to remove non-existent songs on Media Monkey android.

Deleting a song will turn that track grey on media monkey android. I’ve uninstalled then reinstalled, cleared the data and the cache, and yet I can’t get rid of those greyed out songs.

Either version: mobile or desktop, Media Monkey is very clunky. To really turn your music collection into something more than selecting music by it’s default sorting options [artist, name, genre, album, and some others], you’d need to turn Media Monkey into a life sucking major hobby.

Even in making a simple playlist, I just find songs then copy/past songs into a new folder, because songs in a folder can be easily moved to other devices that doesn’t depend on having Media Monkey installed on it.

I dump everything on a NAS running plex. And have a mixture of chromecasts (where I was lazy) and raspberry pis running plexamp (where I wasn’t). I’m all about getting the bits to a DAC as cheaply as possible, and spending the money on DAC onward, where it can make a difference.

For my offline music library I manually edit the tag/info/metadata from Oto or Musicolet.

Then I use Oto Music Player to download synced lyrics coz it can automatically download the synced lyric with one press of a button.

Then I use Musicolet to download album art. I manually download HD image for album art from google (usually from Apple music).

Now I have 1000+ meticulously organized FLAC files, outside that I still have many music files that not tagged properly.

Edit: All that files already organized by artist/album artist per folder. Then I manually transfer all that edited file to my external drive for backup.

I mainly use Retro Music player from my Android phone coz it’s simple and pleasant UI. (Tho I hope Retro can have all that Oto and Musicolet feature I mention, plus Hiby/UAPP bit perfect feature).

Here is what I do…

​

Folder per Artist, Sub Folder per Album (sub folder naming: % Year % - % Album Title %). Music file naming: % Artist % - % Album % - % Track Number % - % Track Title %. Track numbers always have leading zero, no fraction numbering that Apple does. Always embed album art highest quality. Meta data stripped of info and re-labeled per the file name with addition of genre and year.