It's a shame it appears as if I'm wearing a cowl without one. Any reasons why? The guild master wore one when she hired you, so why won't it appear on my character(s)?

She might have a unique version of it. Maybe somebody who kills her in the shack knows.

It's a bug. It works for the females (that are not "beast" races) but works for no males. Regardless of race.

I think it's broke.

I killed her in the shack in a playthrough, so I know that it doesn't work for any of my characters. I played as a Breton, Orc, Altmer, Kajiit, and Argonian. The argonian, orc, and altmer all finished the db questline, and the kajiit "declined" their offer.

It is a graphical bug similar to the Duster from Mothership Zeta in fallout 3 (they chose the wrong skin for the file... I know it also makes me too)

That's a shame. I'd rather work for ANY other assassin organization, but regardless the DB gear looks absolutely awesome Seriously, duel wielding [spoiler[ the blade of woe and mehrunes's razor [/spoiler] is awesome. A mod is in order, yes?