I caught them all alive, and it was far from the impossible task that most magazine and online reviews would have you believe. You've simply got to know which ammo to use. Thudslugs, Boombats, and Zappflies are the three that usually do more stamina damage than they do health damage.
As for the Lootin' Duke, I bagged him by climbing one of the towers and sniping him with Thudslugs and Zappflies.
The only Outlaw boss battler that I didn't bag alive was Tiny, the armored guy that Meagly McGraw rides. He just dies automatically, I believe.
And actually, if you die two or three times at a boss, a hint will actually come up to help you out with a strategy.
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