I am speaking of ASA and FED rules, I would imagine Pony is the same, and if not I am sure someone will correct me. Flex/DP can both play defense at the same time, only one of them can bat as they are locked into the same position in the lineup. So with that said, if your DP plays for the Flex, then she has left the game, she has one reentry just as any player has, so yes you can only do this once the second time you take her out she can not return. You can substitute for her and bring the flex position back into the game but original flex can only reenter once.
So #1 is DP #2 is Flex, 1st inning 2 misses 2 balls at 1st so you replace her with 1. 2 now has left the game as her only thing she did was play defense and now she is not doing that. DP has not done anything but taken over defense for flex. 2nd inning you left #2 try again, this has burnt her one reentry, if you replace her with the DP again then #2 is done for the game. Now you can bring #3 (a legal substitute) in for #2 in the flex position, but #2 can not reenter twice. Note, DP #1 still has not had any change in there status as they have never left the game.
Now the other thing is offense, that is the DP's main job. So if the Flex bats they have to bat for the DP and if they do then the DP has left the game. Also if you use a pinch runner for the DP then she has left the game (as with any player) and they can reenter once, the second time you do this (either let the Flex bat or have a pinch runner) then #1 the original DP can not reenter a second time. As with the Flex above #4 (a legal substutite) can enter enter in the DP position but #1 can not reenter a second time.
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