Flagging obsolete comment conversations

Question

I understand the purpose of the flagging obsolete comments, but by nature of the way that comments become obsolete, often short exchanges (or occasionally lengthy conversations) end up obsolete at once. I'm wondering how we (ordinary users with enough rep to flag comments) should handle these scenarios. There are three options I can think of:

1. Individually flag every obsolete comment in the comment thread as obsolete.
2. Flag one of the comments in the comment thread as obsolete, and hope the moderators will read the thread and delete all comments that are part of the same conversation.
3. Flag the answer or question as needing diamond moderator attention with a message asking them to delete the obsolete comments, and something like the first few words of each comment so that they can be identified.

I always go for option #1, but it has at least the disadvantage that you have to wait around for 5 seconds between flags, which is irritating and slow, especially on lengthy conversations - this makes me feel like it's not the intended way for these scenarios to be handled. I'm also not sure whether the people who respond to these flags can see when they arrive at the page that a whole bunch of comments there are flagged as obsolete, or whether they can only see one. By flagging everything at once, am I making it easier for the mod who arrives at the page to see everything that needs to be done in one go, or am I simply filling some flag review queue somewhere with half a dozen duplicate entries and wasting people's time as well as my own?

Also, if option #1 is the best way to go, what's the right thing to do when you are a participant in the obsolete conversation? You can't flag your own comments, so should you delete your own immediately and then flag the other participants' as obsolete? I don't do this currently, because I don't want to remove half a conversation and leave some incoherent nonsense that makes the other commenters look like idiots (especially when I know I won't get any feedback on whether the comments I flagged as obsolete were actually deleted), so at present I just leave obsolete conversations involving me alone. This seems obviously bad, though; what should I be doing?

Answer 1

There are a few ways to handle this.

First, the way to effect widespread change is to not only flag something, but explain why you're flagging. That way when others see your comment, it will stick in their minds. If enough people do this, it'll spread.

1. Flag the 'tail end' comment (or the 'head' comment) (through flag/other) with:

   Conversation between @user1 and @user2 is now <obsolete> / <chatty> / <not constructive>

2. Leave a comment at the bottom @replying one of the users:

   Please edit information into your answer/question instead of/in addition to leaving comments. It's easier to follow there.

3. (or if obsolete conversation):

   Flagging conversation between @user1 and @user2 as obsolete, please put any information you want saved into an answer or the question (as appropriate).

To this point, we've always dealt with comment flags in a cloak and dagger fashion, but maybe if people start flagging and explaining why, there will be some visibility, and others will take those comments into mind when writing their own comments, and help all of us out by moving clarifying comments to the place they belong (not the comment section).

Answer 2

As @Dukeling said:

I mainly use obsolete, and, to date, 99% of my comment flags have been approved. You may need to spend some time looking at the comments you're flagging and whether they are truly obsolete, and whether someone who just popped in can easily see that they are.

On the one hand, the 5 seconds can be a bother if you have thought about what to flag beforehand.

On the other hand, obsolete flags get handled way faster than moderator flags (sometimes within a minute).

If you want faster feedback and a greater chance of success, just flag as obsolete.

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As further info, @MartinPieters said

if a comment has been flagged multiple times, it'll be auto-removed

which lightens the burden of the moderators.