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@Emyr
Assuming your music isn't DRM'd and you can connect to a broadband connection with plenty of upstream bandwidth, Google Play has an app you run on your computer which adds "all" (up to 20k) the tracks it finds to your Google Account, so you can stream them anywhere, or mark tracks/albums "to keep" and your phone will fetch them (has settings for wifi-only vs anytime).
Tracks bought via iTunes within the last 4 years should be DRM-free.