I recently got into vinyl, and what I found was that convenience is antithetical to my music listening experience. The less I have to think about the process of turning on music, the less I think about the music at all, leaving me without any real memories about it. The more deliberate I have to be about my music, the better.
Like, yeah, I can listen to a full album on a streaming site, but I don't. It just doesn't happen, and I can't get myself to change, so I change the medium instead. Might not be the solution for everyone, but I can understand how having a dedicated box for music on the go would be preferable, not just in spite of the inconvenience, but because of it.