I was going to edit my post to be more clear on the 2nd part that you added, but decided not to.
He's botting his f2p account on the "flagged" IP and then his member accounts on a "fresh" IP.
So he's either:
1) Getting very unlucky and is just in the wrong place at the wrong time or his script isn't that great that he's using
2) The "fresh" IP isn't actually fresh.
I'm not saying my personal experience is 100% the same as everyone else, but if the IPs are actually fresh, then my experience is usually how IPs get flagged.
Edit:
I know what you mean though, just seems a bit more logical than only claiming an IP is flagged for no reason.