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Since you're looking to handle all the bookkeeping for her using Calibre, I think you might be better off with a Kobo device, since it has the best Calibre integration and out-of-the-box support for sideloading. You could even enable sideload mode to remove the Kobo storefront from the UI entirely, thus reducing clutter that might confuse her.
Since you're using Calibre, you could probably pre-format all the books' CSS for her benefit, e.g. changing the default font size to some huge value that suits her eyesight, so she doesn't have to deal with the font menu at all. This would significantly reduce the amount of tinkering in menus she would have to do, as when you buy a book directly from the store, you have to adjust the font face/size/margins manually for each book, which would probably annoy her. If you're taking care of that behind the scenes to automatically make all her books super large print, she would probably find it easier to use.
I believe Calibre supports syncing over Wi-Fi, but I'll let a Calibre expert chime in regarding how you could remotely handle updating her library for her. I'm pretty sure that the default sync operation tied to the Kobo store only lets you download your recent purchases; it can't delete anything from your e-reader, so if you want to manually add and remove books for her, you can't do that without Calibre, at least in the Kobo world.
Regarding models, you'd probably want the 8" Sage at minimum, as 6" and 7" e-readers can't fit much text on the screen if you're using huge font sizes.
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