Can you still get herpes if the person has no outbreak and only takes medication when there is an episode? And you were wearing a condom?

Low risk. It is possible, but you have been partially protected by wearing a condom. Remember, it is stll possible to get herpes even if there are no visible sores so always protect yourself.
It's possible. But the precautions you list will minimize the risk of hsv transmission as much as possible. Unfortunately, the only way to guarantee no transmission of any sexually transmitted infection is to not have sexual activity with an infected individual.