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Just me, but I would do select players that seem logical, Jeter like you mentioned. A-Rod should be prepared for a move to 1b as well. The other possibility is to look at guys that played different positions in college or minors.
Another thing would be to make sure players have the ability to go back and play positions they used too. someone like Chipper Jones should be able to play a truly pathetic SS. I would also give all DH's a position. Frank Thomas and Jim Thome once played the field, so they haven't lost that skill, they just aren't as good as others on their teams.
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