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I'm sure it's intentional to only allow one report on a user within a certain [unknown] timeframe to prevent over reporting (and abuse of the system).
Once that player had been reported, D will look through the chat logs and find the inappropriate behavior from the time you reported it and probably will find the chat that progressively got worse along with it. I would think your one report at the start is enough as it is notifying D that there is a problem with a user. That first notification is enough for them to look through the logs and see what they can dig up. It's not like they're just going to read up to the minute that you reported it. If anything they'll probably give the same punishment (72 hours) no matter when you reported throughout the ordeal.
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