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I can't speak to jailbreaking. I've never done that with my Kindles. But I do have the Paperwhite 3 and the 4 and I can talk about those. I still use both regularly and while they are different I find it hard to care much about the differences. I think I have a small preference for the PW4 but I'd be happy with either one.
I do have a couple of concerns about the PW3's though. I prefer the cellular versions for a couple of reasons. The new one is 4G and the old one is 3G and with 5G coming I'm not sure how long 3G will remain available. Probably as long as the Kindle will last but maybe not. So the future is more certain with the new one. If you get the Wifi version that won't matter, of course.
The other concern is with the ones they're selling as Wifi versions on Woot are the international 3G versions and that 3G can't be used in the USA. I'm not sure where you are but in the USA but in the USA I'd be concerned that that 3G would always be trying to find a tower and drag the battery down. I know some devices do that. I'm not sure this one would but I'd be nervous about that.
Barry
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