My experience with the exact same firmware version (5.14.1.1 on PW5) with and without jailbreak:
pre-jailbreak I had Display Cover option appear seconds after registering the device to my Amazon account
and post-jailbreak while still on the same firmware and re-registered to the same Amazon account that cover option didn't appear even after days spent online (with ota binaries renamed, and before renaming ota binaries I did the actual registration and gave it couple of minutes online then connected to computer to delete firmware update it started downloading & then renamed ota binaries).
So it doesn't seam to be related to firmware version itself?
When trying to troubleshoot that issue myself I had a hypothesis that maybe it has something to do with that debug flag file being created by jailbreak procedure and I've managed to brick / bootloop that PW5 unit when I've edited jailbreak bridge script to comment out a function call for the function that creates that file (I've introduced a syntax error [empty if.. then block] and thus broke Upstart and boot procedure, it loops even before exporting storage so no can do on the whole "DO_FACTORY_RESTORE" thing) to stop it from recreating that file on each reboot.
Anyways, while I was waiting for replacement PW5 to come other people have figured out the solution for Display Cover option:
https://www.mobileread.com/forums/sh...20&postcount=3
So, you'll need to insert the missing "experiment" info into that SQLite database.
I've done that and it works. Before going that route I've even tested doing a factory reset after jailbreak (since jailbreak script messed about some other database file (appreg??, whatever is in device & firmware specific zip "payload" used by jailbreak script) to check if that clears problems with that missing Display Cover option and with Goodreads... and no dice : Display Cover hasn't appeared so I had to enable it myself via database edit.