Ambrose Guardians have a chance to drop one, and once you have access to Ambrose City, there's a shop that sells more and will buy any extra.
There are three optional Maids - one's in Adhauga, one's in the East Swamps region map, and one's in the Ambrose Estate kitchen.
Yes, it's possible to lead the Order, though it's difficult. The vote is based on all sorts of criteria from when you visited the Estates of the other members. Giving it to Archibald isn't mandatory, but it's the best way to not have him kill you if you didn't do well enough elsewhere.
And no, you can't advance time without advancing the story. Not without cheating, anyway. You can get more Silcrow by looking for Holds, though.
Sorry for the slow reply, holidays have been very busy.
Yes, that's Iris. You can recruit her by talking to her, giving her a gift (you'll only get the option if you have the correct item available, which is difficult to do when you first find her there), then find her again and navigate the next conversation.
And yes, it's possible to get an alliance without giving up anything, though it's very difficult. It involves doing things throughout the game, the most repeatable of which is completing events at Big Dick's.