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This may sound a little half baked, but have you considered rerouting a trainer battle as pointer to Mom?
I'm personally trying to figure out how to make battling Rivals bear different pokemon sets based on the outcome of your previous encounter. (Lose becomes Set A and Win becomes Set B).
Maybe there's a way that you can script it so that she gets stronger after every battle like with trainer rematches. You would just need to study how that works as is within the code. You can always set the Payout amount with each trainer you face in Gen3Tools and AdvanceTrainer.