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Love this idea, particularly the roll at merchants. I have a similar thing with gear in chests, roll a die (although I use MS Excel) and if it's 1 the gear fits me, if it's 2 it fits my follower, if neither I sell it.
Ok, ok. So... if the guards are clearly not letting the Alik'r into the city, and indeed arresting those who sneak in... why wouldn't Saadia trust them with the information? And saying "Jarls can be bought" - can you honestly see Jarl Balgruuf being paid off by mercenaries? Her story just rings...
Gotta add something to this. I've played through several times now, helping both of them, and never wronging a Thalmor. When I've helped Kematu I've been attacked by a Thalmor execution squad - WITHOUT ANY OTHER PROVOCATION. This has never happened to me when I've helped Saadia. This is enough...