It really depends on what your favorite game mode is. Personally I get the most value out of WOH, so I always try to make sure I have 3-4 good WOH guys, two for each side of the plate.
I usually do not prioritize certain positions but if you are choosing between OFs and Infielders, better to level the infielder. Also depends on your keepers and My Legend and what positions they play.
You may want to level at least one pitcher too, but I’d start with hitters.
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