I used the T2 for a while, though not on mac.
The Evernote functionality should work ootb without you using the software, though I am not to speak there, I'm a tad paranoid when it comes to cloud services :E).
Calibre itself works as far as you want it to.
You can copy the books you crrently have on your device (I held my entire 3,5k books library on device and ion sync with calibre, you can download books from your local ebook store, add them to calibre (unless they use some method of DRM) and them push them to your device...
Basically you can wrap up everything around calibre but the firmware updates.
And the only thing calibre changes, is the ebooks when you move them around.
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