If you are hoping for the other team to make a mistake at the MLB level, you are really desperate and playing with fire. I would not send a player unless I thought he could beat the throw. You can't count on the other team crapting the bed.
I’m not saying you count on it, but it definitely should be taken into account because these things happen a not insignificant account of the time. I’ll put it another way: If the only way that the guy is going to be out is with a clean field and exchange, a perfect throw and a perfect catch, you probably should be sending the guy.
I don’t have a huge problem with the Howie send. I don’t think you can hold a third base coach responsible for a guy getting hurt doing something as routine as rounding 3rd base. The Adams one was dumb though because the guy had sustained an injury in that game and was limping.
And if I know that Ramos is a crappy fielder, then why can’t Hendley know it. Maybe that’s why he sent the guy?
Point is, you should be aggressive sending guys except in a very rare set of specific game situations. Most people are not aggressive enough. And human have loss aversion. So they perseverate on the run lost when the guy is thrown out at home and not the one lost when the guy is stranded on third.