A:Answer I can answer this question from firsthand experience.
Yes, you can drag and drop entire playlists, individual songs, albums, artist collections, directly from iTunes on the Mac.
Here's the details... you can only do this after downloading the Sony app from their website. It's a really basic application that becomes the place you drop the songs onto, and it converts some of the unsupported formats to what will work with the Walkman. You can also set the conversion settings in the Sony app to save space on the Walkman if you want to. The download link is included in the user manual. You can find the user manual on the Sony website if you want to check out the software before you buy the Walkman device.
What formats will work with the Walkman? Here's what I've tried so far: M4A, ALAC, FLAC, MP3, WAV.
What formats will not work? I have found that the protected type files will not work. For example, like 10 years ago I bought some songs from iTunes and those are protected format, meaning I have to sign in to iTunes to play them, and so they will not transfer to the Walkman.