Thanks for the quick replies!
I guess bricking it is the main concern, as I genuinely like the device. On the other side, I almost bricked it after transfering a few faulty documents to it, so the danger is always present. I don't have a serial cable, but acquiring one shouldn't be a hassle. At any rate, having the rescue pack could be a life saver; as you say, the paperwhite is prone to faults.
In regards to your suggestion, knc1, I did read several pages and posts of various threads here - but I did not know about the three more specified ways of searching for posts. Thanks for the tip.
My secondary concern about the Kindle is in regards to theft. I mentioned Prey because I use it on my laptop, and I have something similar working on my phone. Guarding against theft may not have any foolproof methods, but I usually feel more at easy knowing the applications are running in the background. And finding the device via a website usually saves me some hours searching for where I left it.
I'll read a little more before going ahead with the jailbreak, but it would certainly appear to be beneficial.
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