Leaving "that" in is fine.
Omit "should" from all of the sentences.
1. Ann commanded/ordered that he (should) go there.
2. Ann suggested/proposed that he should join the club.
3. Ann insisted that he (should) wash the car.
4. Ann requested that he (should) go see a doctor.
5. Ann decided/determined that he (should) go to Chicago with her.
6. Ann desired that he (should) come back early.
(Are they all grammatical? Can we omit 'that' in each sentence?)
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