I just started at season 1 again and am on episode 5 or 6 and realized that Sawyer's not as big a jerk as I thought the first time. he did collect a bunch of stuff, but the two or three times people said they needed something, he'd just ask them to say 'please' and then give it to them. He never actually made them give anything. Of course he did trick Kate into giving him a kiss, but he never actually had the asthma medicine and never said he did. He was just being his lovable self there!
That's true...but I mean that he never tried to make people really pay for things or trade important things...he'd just give it with his smirk. He's certainly a bit of a pig ( as Kate called him) in the first half of season 1, but not as bad as I first thought. Also, Locke is such a great philsophical warrior in the first season...reminding me of everything I use to like about Picard. I think both him and Picard became less interesting characters later on (Picard in the movies is the Picard I mean).
No, he wanted to be 'punished' for being a 'bad' person. He's the anti-hero to Jack. He also wanted to prove to Jack that he wasn't perfect (making the decison to torture Sawyer) and he wanted to prove that to Kate too. Now he's just the big damn hero period