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1) and 2) are trivial.
As far as 3) is concerned, calibre needs a way to convert HTML+OPF files (preferably recursively) into .imp. It has no problems calling an external binary to do this (it calls pdftohtml for example and used to call clit). The problem is that whatever method is used needs to be cross-platform and distributable with calibre (so using wine for example is not really an option).
4) Is not so crucial as you can use the save to disk functionality to put them into a folder from where the server programs can automatically sync them.
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