I have Plexamp on my phone configured to automatically download the “loved” album (songs I’ve rated 4 or 5 stars). It automatically downloads songs I add to the playlist. My library is too big to download it all to my phone (most songs are in FLAC format) so I’d need to download a curated list anyways.

This seems to work well. I’ve used it a few times on flights or when I’m in a hotel room with spotty phone coverage and no wifi.

Ah, then musicbee might not be for you. I’ve managed my own songs for at least a decade the old fashioned way so it was easy to import and move my songs around to other forms of media apps. You can however copy and paste the Playlist from iTunes to musicbee. You don’t have to manually add all the songs to the playlist from your library.