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Originally Posted by Daephex
Here are my needs/requirements:
I want to be able to use Calibre easily with the device.
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Calibre can be easily used to transfer books to any device currently available. If you mean that you want to manage collections then Kobo is most likely the direction you want to go.
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I do not want to deal with ads, and am seriously upset that ads are even a thing on ereaders.
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AFAIK Kindle is the only one with an ad option, but it's just that - an option. All of the models are available with or without ads and the with ads models can easily be converted to no ads for a fee.
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I don't wish to have to jailbreak a device. I'm amazed these simple requirements are so difficult to satisfy, please help! 
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Which requirement exactly are you finding difficult?