Sorry, didn't realize it was going to be one of those kinds of things. Most of the stuff I saw was just to move between streaming services.
If you're spending time looking for something and trying it out, I'd just drag them to the phone as you said via USB and recreate the playlists. Only because by the time you find the software that does that specific thing, you could just do it manually. I suspect to do exactly what you're looking for would probably be some kind of scripted thing rather than a piece of software.
Or, if they run in the same sequence each time, you could use an app like Audacity, play or drag the files of your playlist into it, export the file as the playlist name.
As far as the Apple stuff, Google and Microsoft do similar things. They all want you to use only their stuff.