I have played 10 or so games and I am loving him.
Firstly I think there is no point bringing oathkeeper, especially if your spending it in the first turn?? Stick up does the same thing and you will be using it more so might aswell save yourself the trouble of carrying around more upgrades for no point.
He needs a limited upgrade for the extra (0) but more importantly the passive ability on marker pick up, depends on whether you need more attacks or more interacts on which one you choose, don't change during the game as you lose the passive ability while upgrade cycling the limited ones.
The third upgrade will depend on how you play, if you like oathkeeper (for later turns maybe) or survivalist (my choice), hail of bullets only if there isn't cover already and that helps with moving up the table.
General = Stick up, Highwayman, Survivalist
Schemey= Stick up, Black Market, Hail of Bullets
Damage = Highwayman, crate of dynamites, oathkeeper or stick up
