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I've had a Kindle Voyage for four years or so now and a little over four years and just bought a Kindle Oasis 2 when the 32 gb ones briefly went on sale for $150. I signed in through wifi with each of them just long enough to register them to my account and make sure the dictionaries I wanted were downloaded to the device. They've been in airplane mode ever since.
I use Calibre to load any books--even ones I purchase from Amazon to my readers. I keep a large number of books on each (>1000) and don't have any problems reading and finding what I want to read on each.
I also have a Kobo Aura One and a Kobo Forma. I use all four of these readers regularly.
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