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I would like to suggest the possibiliity that the problem is not software per se but of corrupted data.
For example, I recently discovered that about 60 book purchases (my earliest) did not appear in item search or viewing ALL listing (Voyage). My other Kindle, also running 5.8.9, did not have this problem. I suspected some kind of data corruption, and after a Reset, it has gone away.
Reset requires some preparation to make it easier to restore the content you want to have (I created a collection with the downloaded items, then after the Reset used that to restore the cloud content). But at some point I think it is worth a try to see if it makes flakiness go away.
There's probably a more 'surgical' way to clear cached/corrupted data but without having detailed information about where it is and what it does, it may be more trouble than it is worth. Reset is pretty much guaranteed to get your Kindle back to a known baseline state, from which you can attempt to reproduce the issue.
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