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1) Yes. 2) Possibly.
1) Find where your library folder is using Tools->Options->Content (probably "Documents\My Kindle Content") and put your mobi files you wish to "sideload" in it.
I'd say that double-clicking the mobi file in Windows File Explorer will do the same thing, but it appears that newer versions of K4PC and some newer MOBIs may not always work that way anymore.
2) someone with a device that can synchronize and archive personal documents will have to handle that question.
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