Hey Curtis,
I'll chime in on a couple of these...
(1) Bringing the outfield in is done with less than 2 outs, and you can't afford a runner on 3rd, or a fast runner on 2nd, to score. Usually late in the game, pitching team tied. The thinking is, that if the ball is hit shallow, you have a higher percentage of throwing the runner out at home. (Either single or sac fly.) There's no point in playing the outfielders deep or normal, because the run will most likely score anyway, so the only chance is to play shallow and hope for a pop-op or quickly hit line drive hopper that gets to the OF real quick.
(2) I usually do it starting in the 8th when I'm up by a couple of runs. Up by one, I won't take out any of my best hitters. But that's just me. Probably a lot of differing opinions on this one.
(3) Bringing the infield in is really just done for specific at-bats with less than 2 outs. Much like the OF, it's when you can't afford a runner on 3rd trying to score on a ground ball. (Usually a tie game.) Your goal is to hold the runner at 3rd. The belief is since you're closer to him and to home plate it will be easier to "encourage" him to stay at 3rd or to throw him out at the plate. Once you get a second out, you would set the IF back to normal.
Of course it's also a risk since the IFs have less time to react to a sharply hit ball, so the chances for a single increase as well, but you do it because you basically believe that any ground ball that scores the runner will result in you losing the game.
(5) Holding runners has a lot to do with stretch mechanics and how comfortably a pitcher can pitch from the stretch, rather than a full windup. It sounds like you managed that scenario the way it should be, but didn't get the expected result. I'm not sure what algorithms OOTP could possibly have to account for stretch and wind up pitching. My guess is it just cuts down the # of steal attempts, but might affect the pitcher in some negative way?
(6) I use my trash guys in a game that's (depending on the inning) considered out of reach in either direction. It gets the guys some work and keeps the better relievers rested for tomorrow. Of course if I end up losing a couple games this way I tend to change that philosophy.
