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I'm not sure why you think reading something book-length is important but here are my two cents...
I agree that starting out short is the way to go. IIRC Kobos come with Pocket Pocket integration, so you and your husband could start by moving some reading from the internet onto the ebook device. Even if you don't have something like Pocket, you could simulate it using Calibre (or at least you used to be able to, I don't have experience with modern Calibre).
Second, for fiction, Amazon is chock full of self published pieces of all lengths from short stories to novellas, most often priced very affordably. You could convert those to epub for your Kobo.
I've been an avid reader from my earliest memories so I don't have anything to say on the converting a non-reader to reader part.
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