What's your workflow for songs to DAP?

Wife got me a Hiby R1 for our anniversary (and some Truthear Hexa's). And I'm curious what your guys' workflow is for getting files onto/organized on a DAP?

I have my music library on a server, I run droppedneedle, and have it setup with Plex/plexamp(or navidrome/Symfonium) for streaming.

Currently, I've just copied my music folder over to the SD card in a card reader. But, I'm seeing the positives of playlists, as well as an easier way to copy everything over.

Probably going to put Rockbox on the R1, not sure if that changes anything or makes things easier?

Thanks!