Why report the same user twice? Because you forgot adding more examples? If they go look into his contributions they will surely check more than one episode and they will see what's happening.
Of course you can report for multiple episodes. There is the "Other" field on the bottom, where you can give any number of links etc.
If you don't report from the flag in his profile page but you make a Help request, then you can also include screenshots, and write follow-up messages with additional info that has cropped up.
See the screenshot of my report in help center. I included a screenshot. And, even if the case has been closed, you can still write a follow-up. In your case it won't be closed yet, so you can post additional info. But this is ONLY if you did it through the help center, not through the flag on the user's profile page. That form is not versatile at all.