1) Yes.
The Special Offers status is contained in Amazon's database. The Kindle only has a local copy.
2) No.
The only way to Jail break 5.8.10 is by using the serial port access.
(Have you even tried to read the introduction to the current jail break?)
3) Most likely answered in the current jail break thread, the first post of which you should now read:
https://www.mobileread.com/forums/sh...d.php?t=275877