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Batteries do not live indefinitely just because they are not used.
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In fact, batteries in many of today's devices will fail earlier if you don't regularly use the product. I've been using my Kindle keyboard for 3 years now and no battery issues yet. I use multiple ereaders (I use 3), so I see no issue with buying another. I don't see why the NEED to jailbreak (I don't even know what it does), but that's your personal need then go for it. Even if they stop upgrading the software in future years, so long as you continue to remove DRM from ebooks you buy and store them in Calibre, it won't be an issue.