[Qerub]

You don't even have to buy the songs on iTunes to have Apple stream them to all your devices. With iTunes Match (included with Apple Music subscriptions or available stand-alone) you can build a "cloud library" from local files: https://support.apple.com/en-us/HT204146

[lloeki]

Watch out, iTunes Match and the Apple Music match service are subtly different: the former will match to (and failing that, upload, transcoding to AAC 256 if needed) DRM-free versions, while the latter will match to/upload for sure but downloading them on another device (or the same if you delete the source file) will get you a FairPlay protected file.

[geerlingguy]

This is how I manage my music library, and other than the fact that iTunes Match could potentially 'eat up' a song you import into it if it matches to a different but similar-name/time track, it's been great.

I always keep a second copy of all my original rips just because I'm worried that kind of thing could happen—if not immediately, then later on when I sync a new computer and iTunes Match finds some new song that conflicts.