[Syd Thrift]

Learn OF
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Description: Center field is, according to the good old defensive spectrum, the toughest OF position to play and the 2nd toughest overall. As such, do not expect it to be easy. RF and LF are learnable.
Player Skill: Work Ethic or Speed, whichever is lower
Limitations: Only applies to infielders, since OOTP does not currently give most of these types any ratings in the OF at all. If you want to teach a LF or a RF to play CF, play him in center field. You must choose one of the three OF positions to learn; that will be the position where your experience is added.

EDIT: If you want to teach an OFer another position and you have a good coach, run the tables but ignore everything except the experience and the batting ratings changes if you go bust.

Bust: No ratings changes in the OF, -20 AK, -10 POW, -10 GAP
Failure: +25 OF experience, OF range = IF range -40, OF error = IF error - 75, OF arm = IF arm - 100
Ignore: +50 OF experience, OF range = IF range - 20, OF error = IF error - 40, OF arm = IF arm -75
Good: +100 OF experience, OF range = IF range, OF error = IF error - 20, OF Arm = IF Arm - 50
Excels: +150 OF experience, OF range = IF range +20, OF error = IF error, OF Arm = IF Arm - 25
GREAT: +200 OF experience, OF range = IF range +40, OF error = IF error +20, OF Arm = IF Arm

Learn IF (as OF)
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Description: OOTP doesn't generate IF ratings for OFers, so this is necessary. For the most part you are going to need a Gold-Glove quality OFer with strong range, hands, and arm to play an infield position at all. I've found that if you're going to hide anybody at one of these positions, hide them at second base. This is especially true during the dead ball era if you've properly adjusted double plays; the pivot rating comes into play so rarely that you can make it into a real offensive position pretty easily (this, by the way, is what they did with the position IRL until the 20s - this is why 2 of the top 3 2B of all time played a good chunk of their career during this period).
Player Skill: Work Ethic
Limitations: Only applies to outfielders, since OOTP does not currently give most of these types any ratings in the IF at all. If you want to teach an IF to play 3B, play him at 3B (preferably in the minors). Catchers will have a separate skill to learn 3B for you Charlie Moore wannabes out there. Applies to the positions 3B, SS, and 2B. EDIT: And 1B.

EDIT: If you want to teach an IFer another position and you have a good coach, run the tables but ignore everything except the experience and the batting ratings changes if you go bust.

Bust: No ratings changes in the OF, -20 AK, -10 POW, -10 GAP
Failure: +25 IF experience, IF range = OF range -60, IF error = OF error - 60, IF arm = OF arm - 80, Turn DPs = 20
Ignore: +50 IF experience, IF range = OF range - 40, IF error = OF error - 50, IF arm = OF arm -60, Turn DPs = 35
Good: +100 IF experience, IF range = OF range -30, IF error = OF error - 30, IF Arm = OF Arm - 50, Turn DPs = 50
Excels: +150 IF experience, IF range = OF range -10, IF error = OF error -10, IF Arm = OF Arm - 25, Turn DPs = 75
GREAT: +200 OF experience, IF range = OF range +10, IF error = OF error +10, IF Arm = OF Arm, Turn DPs = 100