A reminder, half cocked kindness causes a hell of a lot of problems in LC and LOR.
If you bring someone to the edge of ruin and let them leave alive it will ruin you in turn.
Did for Ayin with Garion, did with Roland for Jae-Hon, and mark my words when The Head falls it'll because they didn't tie off a loose end.
Those...actually aren't good examples.
If Ayin hadn't let Garion live, we wouldn't of gotten Binah. If we never got Binah, no one would've been there to help Roland work through the last Relazation he needed before the end. Which means we likely wouldn't even made it to the ending, cause no one would've given Roland the Therapy he needed to be able to forgive Angela. Nor would anyone have been there to save his and Gebura's asses at the end, meaning him and Gebura would've died there.
Roland didn't let Jae-Hon live on purpose. He did try to put the man down for good. It just so happens he failed cause people in the city run the gamut from "Die to a stab wound" to "Need to be fucking dismembered" to put down.
And sure, the Head is going to pay for letting us go...but they did not do that out of kindness. They did it cause they could. If anything, it was to show the rest of the City what will happen to you if you ever reach a point where you can actually threaten the Head. That being, they'll just fucking kick you out. The Library is a special case cause it's completely self-sufficient and can handle creating its own resources to survive in the Outskirts. Not everyone else can.
As far as the rest of the City is concerned, the Library has been handed a Death Sentence worse than anything the Head can come up. After all, everyone knows the Outskirts are awful places to be and don't have any of the resources the City has.
And who knows, this might've actually been they're plan all along. These are the same people able to keep the Index, people who follow the literal Precognitive Will Of The City, in check and who would be able to get a handle on things like White Night if they ever got out. There's no way they didn't think this through.
Edit: Also, just to clarify, I may constantly be against upping our Empathy, but that's not cause I don't think it's important nor that I don't think we shouldn't do it. I just think we should wait on it. Specifically, until we get a good amount of points into Fortitude and Justice.
Fortitude gives us the outer strength and power to back up our words, thus allowing us to be empathetic without dying.
Justice will give us inner strength and power to follow through on our words, which is lead to others following us and listening to our words, as well as help us see the bigger picture.
Once we have those at a good level, which I think getting Fortitude to Rank 3 would be a good stopping point for now, then I think we can start upping our Temperance.