Qobuz.com fits most of your requirements:

> 1. Very agnostic: Needs to work on: SB3, SB Boom, SB touch, iPad,
> Android phone, plus Mac and PC desktops 
I have run the service on SB Boom, Touch, Android, Windows Desktop. I'm
pretty sure there is a client for Mac and iPad/iPhone 
> 2. Supports off line dowloading
I have used offline downloading on Android and Desktop. When downloading
flac on desktop (you can stream flac on SB and Desktop), downloaded
files are encrypted. Did not check mp3 on Android. 
> 3. (Not sure if any service does this) supports offline downloading AND
> moving the mp3s to other devices (i.e. ipod classic)
I'm not aware of such integration. Also, downloaded desktop flac are of
no use outside of desktop app, again, I'm not sure of mp3 on portable
devices.
> 4. Has the ability to support 2 users on at the same time.
Supports multiple users.

You can sign up for a free month and try it out, there are 3 plans to
choose

mp3 all
flac classical only
flac all

It also depends what kind of music you are after, please check the
offered cataloque.


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View this thread: http://forums.slimdevices.com/showthread.php?t=98798

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