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@fesja: All those negative reviews you posted are complaining about how "ugly" the user interface is, not about its usability. And about 90% of those will be on OS X, where the interface is admittedly ugly, as it doesn't use native toolkits to render itself.
Here's the typical calibre start use case:
Run calibre, answer two or three simple questions in the Welcome Wizard (@kiwidude: you're desire to add more questions to the Welcome Wizard complicates precisely this use case). Then calibre starts, the very first, very promininent button you see is Add Books. Click it and you can add any ebook file you like. If you're used to using drag and drop instead, calibre allows you to do that, too. Plugin your device, calibre tells you it is plugged in. There's a very prominent button labeled Send to Device. If the book is in a format the device doesn't understand, calibre auto-converts it for you. It simply isn't going to get any easier than that.
Now there are things that are complex, and that could be stand to be simplified, metadata plugboards, changing the default author sort algorithm, and finding preferences in general, connecting to MTP devices, setting up the content server.
But, you need to realize that those are complex things by their very nature. The "simple" apps you are talking about from Amazon and Apple will not even let you customize these kinds of things, let alone provide a simple interface for them. Those apps are simple because they are dumb. They force everyone into a one size fits all, highly streamlined, but completely un-customizable workflow.
Now, I choose to respect my users. I believe that most people will, when given the chance, appreciate having the ability to do more complex things, as long as the basic use case is as simple and painless as possible.
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