Well, being a highwayman isn't too hard but being a thief is because most chests are locked.(note: You need a villain application to do anything villainous)
Aye, most of the people that were in the FOA when Aeriel's Keep was new have left us without notice. I will ask Maur to set up a activity check.((I think the activity check should be on a different thread so we can edit the OP))
You should make his hood and mask in the hat layer(if you haven't already, maybe novaskin is making it look like it isn't)), it will have more depth and look more realistic.