I've never been able to capture all outlaws alive - I believe I may have come close, but I disctinctly recall being extremely frustrated with at least one of them, to which end I just said "fuck it" and killed them.

Alcar...

The Easiest is the first boss, just shoot a bolamite and bounty!

Every one of them. I like to be merciful, as the kind get more money. Like in reality. I get my doctorate so I can help people, and what do I get? A sense of achievment and a shit load of money.
The Beatles gave us their music, and what did they get? Fame, women and a shitload of money.
Stranger bags an outlaw alive and what does he get? A shit load of money.