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Connect/Share->Connect to folder then use Send to Device is exactly what I am doing.
And no, havn't tried Windows safe mode.
But I tried something else that worked (so far): I deinstalled calibre and installed the 64bit version (not sure why I was running 32bit in the first place).
I did this yesterday afternoon and did not see any error so far.
In case it is really a memory error I hope it now will not happen at the maximum 2GB of 32bit processes but much later. So far this worked!
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