I have had a Spotify premium account now for six years, and yet I do not have one iota of the emotional connection with Spotify that I have for my old iPod. I also have a much smaller Spotify library (thanks to to the 5,000 song cap), yet I know it much less well than the iPod's.
Part of this is because of how I curated the iPod library: mostly through sharing mp3's in high school and college. Everyone then tried to limit just how much they individually pirated from Kazaa and Limewire, but if Henry had albums from a dozen new artists he suggested you would like, you didn't ask how he got them. There is a relevant SMBC comic for my nostalgia, but I think this was just about an ideal music market from a consumption standpoint. The marginal dollar cost was zero, but the expectations to identify good music and reciprocate to keep participating in the shared economy were high.
I do not see how Spotify can ever recreate this system, but there are other ways it could improve. There is an information overload with any established artist. You can either listen to the top five songs, or wade through a dozen random live recordings and greatest hits compilations to find the album you want. And bless your heart if you want to queue a 1992 recording to follow from 1998. Everything about Spotify seems to want to recreate a browser experience, and yet it still doesn't have tabs. Why have so much music (and information about the artists) worth exploring while making it so difficult to explore? I also do not need to see album art thumbnails or headshots of every artist, and I especially do not need to see them if it makes loading my library take thirty seconds longer.
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