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It's all content owned by me but it was ripped and cataloged (which took fucking aaaaaages) manually.
For Movies & TV Shows I used rippit, then batch processed them through Handbrake using an automater flow. Then they were tagged etc using iDentify.
All music is stored in ALAC as it plays nice with iTunes / iPhone etc but it can easily be converted back to FLAC in the future.
I've never bought anything from iTunes (apart from phone apps).
Soul
Did you buy all that stuff off iTunes or were they 'purchased' elsewhere?
My Apple TV won't sync my movie library at all, I have to use Plex which can be a bit hit & miss at times...