She sits across from him for the beaver-shot, why else?

Yes. This is a crime family, they have no sense of style.

Gotta keep sleepy joe awake some how

(Probably not appropriate)

Appropriate for the setting? Probably not the best choice.

Appropriate based on her age...? Seems the norm.

Meh, it's a little short but not sleazy in any way. There is plenty of stuff to rip this admin apart on, this ain't one of em.