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As this is a windows crash the chances are that there won't be any debug window output from Calibre.
Perhaps it is a font thing - have you tried choosing a different font in the generate cover dialog? My setup is the same as yours in terms of Win 7 64-bit SP1, but I've never had this crash. It looks like an issue in the Magick libraries which is not plugin code and beyond my expertise. If you can figure out any scenario to replicate it then perhaps Kovid can take a look.
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