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It's Working!
Well, I don't understand why, but the Microstudio Play function now works, but only when I have also opened up Adobe Pagemaker 6.5. If I close Pagemaker, it stops working; when I open it up again, it starts working! I've tried a slew of other applications but only Pagemaker seems to achieve this magic. Maybe Pagemaker is capturing some piece of RAM that Microstudio can't handle or some *.ddl is being activated. This is one I'm never going to figure out, but at least I have a workaround that now lets me use the Play function.
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