I love that $10 for monthly access to basically every album ever on demand is "a bit high". I remember dropping $16 a pop on CDs/Tapes at Tower Records back in the day, probably bought at least two a month...
In terms of your issue with iTunes cover art, didn't they announce some thing where you pay a flat fee and is basically matches all of your illegal music with legal one when iCloud was introduced (I never tried it just remember the keynote vaguely)
You're recalling iTunes Match, the service which allows you to upload/match your iTunes library and access it across multiple devices. This service is $25/year.
However, you can have iTunes download album art (even for albums you've imported and haven't bought through iTunes) for free. You can just select every song in your library and the right-click and choose "Get Album Artwork" or something like that. It works decently for music you have somewhat accurately tagged (at least a correct artist and album name). Again, this fails for a lot of electronic music though.
"Again, this fails for a lot of electronic music though."
It also fails for classical music. But since I ripped CD's I just scanned in the cover and added the art. Trust me, it was time consuming. But there is hope, iTunes has added much more classical/opera recently. So changes are, if I had to do this all over - a lot of the art would be available from iTunes.
In my collection, The album art matcher is quite bad. Stuff that's tagged correctly and well known (e.g. Led Zeppelin) comes up with the wrong (but related) image. Where it really falls down are compilations, I think it's running about a 20% hit rate on those.
Yeah, I think it's incredible that he thinks $10 is too high. Perhaps he means '$10 is too high for a limited and poorly organised music selction'.
I would have no problem paying double that each month for Spotify, and upwards of 3-5 times that if it had a music catalogue and organisation structure similar to iTunes. Granted, I value music more than many people, but $10 is what a cheap lunch costs, for unlimited music on demand.
I have iTunes Match a shot - it was ok but it didn't get all of my music fixed and it didn't change any of the fundamental issues I have with the whole workflow.
Find artist
Download/buy albums
Listen to songs, rate, put in playlists
Sync to devices (this it solved)
In terms of your issue with iTunes cover art, didn't they announce some thing where you pay a flat fee and is basically matches all of your illegal music with legal one when iCloud was introduced (I never tried it just remember the keynote vaguely)