I think the important parts are in bold here: You cannot transfer your Kindle purchases from your computer to your Kindles via USB unless you schedule delivery using one of the methods above.
My reading of this is that Kindle ebooks with DRM will only have the right PID in them if you first schedule delivery and then download them. Similarly, DRMed ebooks (i.e. almost all Kindle ebooks from Amazon) on an existing K1 (say), or archived on a PC, can't be transferred directly to a K2. They have to be re-downloaded from Amazon first.
This does not apply to any DRM-free content. Since these are not tied to particular devices.
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