I happened to have gotten this achievement very fast and by coincidence while i tried to do it as GrandmasterALK suggested. I was on my way to Nosalida when all of a sudden a woman with a bunch of dudes cried for help. Remember the situation, woman screams, blue dot pops up in mini map and when you get closer the guys start shooting at you, does that ring a bell? So i went dead eye, shot all the guys and then i realized on the mini map that the blue dot changed into a red one. I changed to lasso, hogtied the woman who started that mess, took her to the train track, train was passing (coincidently) and cheevo popped. This took around 1:30 minutes real time.