The problem I have is that my friend is virtually totally blind - he can just distinguish light from dark. So I'm leaning towards using Siri on an iDevice to let him voice-select his music, but I don't want to preclude using some other device/os if it can get him the accessibility to the music - hence ripping to FLAC and then transcoding for the playback device seems like the best route to take. So I'm not sure if using a non-integrated music player is feasible.
Being blind sure sucks. and what makes it harder for my friend is that he's a true audiophile - having had the best audio equipment ($25k speakers & fabulous tube amps) when he could see.