The plot thickens. Yes it does.
I love that response of Pen's to Mercer's protestation against Pen's joining the Legion. It sounds like just the sort of thing Pen would say - few people in Skyrim truly like "Her Highness" Maven Black-Briar.
I'm personally quite curious to see Brynjolf's reaction to the discovery that Pen... "Oh hi, sweetie. I picked up some fresh-baked bread, some Black-Briar mead, oh and by the way I joined the Legion."
Again, you characterize Sjadbek so well. My Sjadbek is quite a bit less scared of the Thalmor than yours is... but my Sjadbek is also the Dragonborn and yours isn't, and that's a pretty big factor.
LO, yep! Pen is like the anti-Maven of a character. She's not impressed by her in the slightest, refusing to give her credit for much of anything since she sees it all as so incredibly slimy. Thing is, Pen is obviously not completely opposed to 'playing the game' as it were, in order to get helpful leads for a much more important cause. But she truly despises her and everything she stands for as far as familial imperialism goes. She's seen it enough back home in Cyrodiil, she's still not impressed now.
Bryn's reaction will be interesting as well. Haha, the look on his face = priceless xD I can't wait to get to that. Mostly it'll be funnier to me since it will more than likely be Mercer who breaks the news to Bryn about it, not Pen herself. Mercer will try to use it as a point against her, but not everyone in the Guild will be keen to look at it that way...
And aww, thanks! That's big praise coming from his creator, so I'm flattered!
Yeah, my Sjad here is a bit more worried for the sake of Pen. He really has zero idea of what she's up to in Skyrim (at least for the moment) and so he's only able to go off of what he sees. I liked how he sorta brushed off the arrest bit but was much more concerned about the Thalmor tracking
her down if anything was slipped. Sjad's adorable.