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Realice INSERTAR con SELECCIONAR para insertar múltiples registros

INSERT 
  MainTable_Option 
  (
  MainTableID, 
  OptionID
  )
SELECT
  d.ID, 
  o.OptionId
FROM
  DodgyOldTable d
  INNER JOIN Option o ON
    (d.OptionVal1 = 'Y' AND o.OptionDesc = 'OptionVal1') OR
    (d.OptionVal2 = 'Y' AND o.OptionDesc = 'OptionVal2') OR
    (d.OptionVal3 = 'Y' AND o.OptionDesc = 'OptionVal3')