Swamped

Every good squad needs a Blade, Leaf, Wing, and Stone.

Captain Long will be the Blade - he can keep the Rider distracted and (more importantly) the Rider can keep him distracted.

Burgundy would be the Stone - Long shouldn't object to sending her out, and having her eyes off of you would allow you to make some extra arrangements.

Darlene Kitey is the Wing - She's familiar with marshguards (having escaped so many times) and has solid intuition for tight situations. She's also terrifying with a mudpike.

Penelope is your Leaf - She's not battle hardened, but she's diligent, determined, and shown quick progress. You've been teaching her a few card tricks, ways of winning games even when it seems you lose. She understands that sometimes a trick or two is important for the greater good.

And, of course there is the matter of the letter she divulged to you.