The easiest way of all requires making a pact with the devil.... I converted from flac to apple lossless (yeah, yeah, get over it, and yes I did keep a backup copy). Everything is now in iTunes. Any stuff I want to buy can be ripped into lossless, but to be honest, life's too short and I don't listen in such a critical environment, so most of it is downloaded, and from itms, so yes, a bit lossy (and doubtless ruinously expensive etc). Anyway, what it means is that I can buy a song on my iphone (or wife's iphone) and it will automatically be added to the library and magically appear on LMS. I can't tell you how much hassle that saves me.
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