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@JonoMarshall
Apple can't tell where your music is from unless it is tagged with their DRM (and therefore bought through the iTunes store), not legally anyways... you're fine.
I doubt they care where your old music is from, but they do want you to consider buying all your future purchases through iTunes, hence the Genius bar recommendations and such like. There is little pint in investing money into finding out how people purchased their music in the past... there's oddles of info out there about piracy patterns anyway. The key will be to grabbing the emerging legal downloads market, which Apple is seemingly mastering at the moment.