It's a cool idea, but the flaws you've pointed out certainly hinder it from being too useful.
Perhaps it could be used as a teaching tool in its current state, showing examples of scouting, prediction, risk & reward, etc etc.
Very cool though! Definitely keep working on it. Maybe you could have Regenerator and Natural Cure be automatic on the pokemon that use them, as the pokemon that do always use them. (No more Own Tempo Slowbro or Serene Grace Blissey running around :P)
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