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Ok, soooo...this is slightly embarassing, but I believe I figured out what my problem was. And because it's really stupid, I'll share so that others may benefit from my embarassment.
So this KT isn't my primary Kindle anymore. I have a KT3 (2016) that is my go-to. I would've been jailbreaking it if I could, but alas the firmware is too new (current, even. Thanks, Amazon!). I haven't used my KT in months, and hadn't needed to download anything new to it in years.
And I've since changed my account password a few times. ~.~;; I didn't remember that the password would've been out-of-date until after I ran a factory reset and had to log back in, and realized I'd never typed the new password into this device. There was no way that it could update my SO settings, because it wouldn't have been able to log into my account. I didn't twig onto it because the offers were still updating themselves and everything was behaving...well, normally. It's a bit weird that it just so happened to reset itself less than a minute after I updated my account, and that first time it went to the standard wallpaper of a bunch of printing press letter blocks, but maybe that's when the system finally tried to authenticate the account again and the password didn't match? I don't know, I can only guess at this point. All I know is that I've started fresh, gone back through everything, and now I see that lovely "The ScreenSavers Hack has been successfully installed!" wallpaper.
Thank you for your help, and for responding so quickly. I would've just kept spinning my gears if you hadn't offered me the chance at outside perspective.
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