Interesting reaction to war... ;)
Gwen's healing - if she gets healed - won't be for a while. You live with the consequences of your actions!
Ami will wear your dictated outfit around the house starting from the next update. Right now she's super busy keeping everyone safe.
Viewing post in Weekly Update: v0.17.6 - the War Map! comments
No, that's going to happen no matter your choices. It's an object lesson to MC that he can't just "wing it" like he's been doing. His enemies are taking things very seriously and if he doesn't step up then the people around him are going to get badly hurt... or worse.
I do feel bad that Gwen and Chloe have to keep teaching him lessons, though. Those girls have not had a great time :P