Not so long a go a user here on Meta Stack Overflow asked how he could prevent getting downvoted. To make a long story short, it turns out he had multiple accounts to evade multiple bans. He finished off the discussion with the admission that he just had to go on creating new accounts and changing his IP address.
Lo and behold, today I commented on a question which was about to get closed and the OP turned out to be this user. How can I be so sure? He explicitly said so within a comment and linked to the above post, stated he had multiple other accounts, before he deleted the question. I flagged it for moderator attention, and it was dismissed as helpful.
That's all fine and well, but it got me thinking. I've raised several such flags before on other accounts, which we equally dismissed as helpful. Of course, I can't see the details, but it seems nothing really happened. Perhaps the OP was already post-banned on those accounts, so nothing really needed to be done. I don't know.
Is there however still a point in me flagging such violations? Whenever we see a user on Meta Stack Overflow ask "Or do I have to create a new account?" when banned, we collectively go "Noo, don't do that. You'll be caught and banned and the accounts will be merged and Unicorns will do terrible things to you when you sleep".
That doesn't really seem to be the practical case however. Yes, we do get tough language in previous very related cases, but on the other hand there have been various admissions that Stack Overflow/Stack Exchange tends to stay away from IP address range bans for obvious reasons. And given how easy it therefore is in practice to evade a ban by creating a new account, should I perhaps simply think "Well, if you manage to stay out of trouble this time, good for you"?
Yes, the OP should ideally bring back the account into good standing, unbanning him/herself by improving content and contributing well where still possible. But are we going to enforce that if the new account is not really doing anything wrong? That is, if the lesson has apparently been learned?
In summary:
Should I continue to flag ban evaders who create new accounts for moderator attention (especially if their current accounts seem reasonably okay), or is there no real point and should I just let it slide?