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I think it depends on which part of the figure you parent it to because when I parent a dress to the "BODY" and then do scaling, the dress scales with the figure. 

Really? From my experience, parenting a dress to the body and scaling the figure down in the first frame will make the figure stretch into it, and if you scale it up it will make it looser. You need to make sure that the figure is 100% in size in the target frame. I can show you examples if you want, but try it for yourself, it's always worked for me.