Excellent question! This is clarified in the FAQ, under 'Wanted'
Dudes are the only card type that can become wanted and gain bounty. If a dude card says it is not considered a dude for resolving card effects, it cannot gain bounty or become wanted.
So in the Hustled + Ol' Howard case, Ol' Howard ceased to be a dude, and thus cannot gain bounty or become wanted.