More Watcher Jessamine thoughts (I apparently lied about switching game focus):
I previously said I thought she'd side with the VTC in Deadfire; after playing her more I now think she'd side with Aeldys's faction of the Principi. (She hates slavery. She REALLY hates slavery and would not forgive the VTC for being complicit in it).
Since she's still in Act 3 of Pillars 1, I've been contemplating which god she'll side with, and I'm leaning Galawain. One, I haven't sided with him before so it's new content. Two, Jessamine is more pro-Dyrwood than I expected so I think she'd be on board for strengthening their souls. It just feels a bit on the nose having the nature godlike side with Galawain.
The faction she sided with in Act 2 was House Doemenel!
Her relationship with Iovara in the past life has been clarified as "friends;" I think the person she was actually in love with was Thaos (though I haven't gone as far as installing the Thaos relationship mod, and also I was not expecting this). Though this does not carry over to her current life. She just fucking hates his guts.
I don't think she's keeping Vela, though she could surprise me.
She's bffs with Kana (there's a reason he gets to run with the girl squad), possibly extending to crush, but nothing ever happens. He's the one that encourages her to take up Chanting instead of just singing, leading to her Rogue/Chanter multiclass in Deadfire.
She's normally on board for stealing things, but was extremely affronted by the guy in Stalwart who wanted her to steal some alcohol from the bar. I don't actually have a good character explanation for that one, so I think the spirit of Poetry overcame me in that instance.
For shipping, I'm leaning more and more towards Tekehu. She's actually not close with Aloth at all, and while she's friends with Pallegina, they have very different worldviews.
The party I'd like to run with in Deadfire is Jessamine (Trickster/Skald), Tekehu (Druid/Chanter), Serafen (Cipher/Barbarian), Xoti (Priest/Monk), and Maia (Ranger/Wizard), although I'm a little worried about that party not having a clear frontline tank. But I want to actually try to get Xoti and Maia together for once!