Well considering I'm the scorekeeper when I'm not playing or if I'm DHing and I'm the one keeping track of stats I often am faced with decisions like this.
If I know a player's ability well enough that I know whether or not he would've made the play it may be tougher on that player. I usually don't change decisions in the book afterwards if I'm not scoring unless someone who isn't used to it is scoring and I know what play it was.
I've been given grief on the stats about someone having more double when they really advanced on a throw or an error, or someone claiming that it wasn't an error or they have more SBs when they really advanced on a wild pitch or PB.
In fact our last game I was scoring and we had a player that came and asked me after he came back to the dugout and asked me "Was it a hit?" the first one was right at the LF hit his glove at his chest and he dropped it then he slid for some reason after and he whined that well he slid so I get a hit. Then his next time up he hits a ground ball that goes right by the 3B he argues well he didn't touch it so I get the hit, but the 3B just missed it with his glove so I gave it an error since the 3B didn't even have to move.
It's annoying when you've got people pestering you to help their stats. Oh btw (and since I don't score when I play the field) while we're mentioning it, only one error all year
, least on the team.