An AZW file's content is essentially identical before and after the DRM is stripped, so all the metadata is still there. Amazon can definitely detect that it is DRM-free and also that it was sold from the Kindle store (as opposed to a MobiPocket store, for example). I don't know if they can tell who bought the original ebook. Note that I have never heard of Amazon actually doing this, but it is technically possible.
Once the DRM-free MOBI is converted to ePub, some of the metadata is removed. In addition Apple has no skin in the Kindle store game, so it is hard to see why they would care where the ebook came from. However, if you have a DRM-free version of an always DRM-ridden title then the DRM has clearly been removed. What Apple can't tell is whether you have bought the original ebook, or got it from a family member, or downloaded it from the darknet.
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