I have iTunes match (£22/yr) which sync’s your iTunes library and its OK (means you can delete local and download 256kB AAC files which are all completely kosher). I also have a chromebook and have uploaded my music there too (Google), for free.
I sometimes stream to the chromebook but I usually use them as two offsite vaults for my music. My iPhone is a pain in that you don’t choose to sync any more, it downloads and caches on demand so if you’re out and about and suddenly want a track you have to get to a hotspot or download over 3G. Otherwise you have to tell the music player to download while at home so it caches.