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On windows there is no good way -- the minimum you would need to do is rebuild calibre from source yourself with debugging symbold turned on and either use windebug or the visual studio debugger or failing those two stick lots of printf() statements into the relevant code path.
Windows is unfortunately the only major platform that makes it really hard to debug crashes -- it is on my todo list to setup some facilities for debugging crashes on user's windows computers for calibre but its a fair bit of work.
Generally with MTP crashes it is typically the windows portable device susbsystem returning unexpected data to calibre. Simply rebooting the device and the computer might fix it.
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