If you pay for iTunes Match, import all of your non-iTunes music into iTunes, Apple will store a DRM-free AAC file (256 kbit/s) in the "cloud" which you can play/import directly onto your mobile devices (without sync/tether).
You only have to pay for iTunes Match when you have new music to import. Once imported it is available "forever."
PS - I ironically used this to escape the Apple ecosystem. You can use it to strip DRM from old Apple DRM-ed music. You import it using match, and it converts it from an AAC-DRM track to an AAC DRM-free one and ups the quality from 128 to 256 Kbit/s.
It gives you the highest quality Apple has for the song, if it's matched. I had a ton of terribly transcoded files that got replaced with 256kbps AAC files. In my reading and own personal testing the difference between 256kbps AAC and 320MP3 is negligible. The only issue I ran into was some stuff didn't full match an album. I would get 10 out of 12 tracks matched, or 5 out of 12. Still for 18K songs I think I only had 100-200 that didn't end up being matched.
Amazon does offer this too but I have no idea how well it works in comparison.
If you pay for iTunes Match, import all of your non-iTunes music into iTunes, Apple will store a DRM-free AAC file (256 kbit/s) in the "cloud" which you can play/import directly onto your mobile devices (without sync/tether).
You only have to pay for iTunes Match when you have new music to import. Once imported it is available "forever."
PS - I ironically used this to escape the Apple ecosystem. You can use it to strip DRM from old Apple DRM-ed music. You import it using match, and it converts it from an AAC-DRM track to an AAC DRM-free one and ups the quality from 128 to 256 Kbit/s.