The sounds pretty damn good (the Naga/Gorgon since you've started figured it out already). Him working part time is perfectly fine since...... Well the only character that works for the Stoneroses full time is Efi and even she is trying to start her own shop. Nancy will just have to make an appeal to ArnoldKylesar1
I've been brainstorming some character concepts. Well, mostly one, but I want to introduce two characters at some point.
One will be another Stonerose recruit. I have almost nothing at all figured out about them. I know they'll be a lot different from Nancy, but they won't be foils of each other like Bogrum/Fergie. Probably won't interact as much together either. For this, I want to play out two very separate lives rather than two friends joined at the hip.
The other I have much more figured out. She's an old Naga/Gorgon sage who runs a magic shop (specialist or general, not sure yet). Large and frightening to the human populace, especially because she serves a Daedric Lord. She gets decent business with the other marginalized populace mainly, and also because of her hundreds of years of expertise.
She's in need of workers after an "incident" scared off her employees, and few are either willing to put aside their prejudice towards her or can't meet her high standards in general. This is where Nancy comes in. I figure after the upcoming Mirage Flower task, whether he succeeds or not, will highlight that he desperately needs proper guidance on alchemy if he's to do this professionally. Through whatever natural progression, Nancy will become her apprentice, and work part-time at her shop.
Not sure if the Guild would like one of their few members being unavailable for parts of the week, but perhaps the promise that he'll use his honed skills for the Guild either primarily or exclusively might sweeten the pot.
I'll be playing as her because I have a very specific vision for how their dynamic will play out. Matronly and emphatic towards his struggles, but harsh when need be. Nancy tends to victimize and limit himself, and those vices are what hold him back from his true potential the most.
She died during the first war, to explain her absence in the Pirate RP.
There can always be a part 2 for the Mirage Flower. There's finding the Flower (which is the mission) and then there's transmuting it to something else. Of course he can pass fail that and it be a thing, but that can play out how it does.
Spoiler: There will be a transmutation part involved in the part 2
It'll be an interesting conversation between Arnold and Nancy though. The Mirage Flower will be a big deal. It's something that appeals to Nancy's skillset