For If I Were a Rich Man:
Easiest to get by downloading the free alternate ending. Play through it on Recruit and kill Dalton. That gets you 75k. Go to the campaign and continue from the checkpoint and you'll be right at the Dalton fight again for another 75k. If you get a little rhythm goin, you can kill him in about a minute just solo.
Also really helpful for Man of Many Masks and any achievement that requires you to buy anything.
Stick that one into the guide.
I used to have a 100% list for my games. Then I ran outta space.