What you need to do is contact Sony about getting that 500 upgraded to support ePub. Without the ePub upgrade, the 500 needs a custom USB driver that does not work on Windows 7 64-bit. I cannot say if it works with Windows 7 32-bit. Once it's upgraded to ePub, you should be able to use the latest Calibre.
But, given that the 500 is for your mom, you'd be best using Reader Library to manage the 500 once it's been upgraded to handle ePub.
And yes, you were correct about not buying it. The screen uses the 1st generation eink and the contrast is quite poor and it can fade in direct sunlight. Also, the processor is rather slow.
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