Etiquette for enormous hand-sorted retagging jobs

Question

We already have general guidelines for when you should just ask a moderator for help in retagging. A system for handling soft retags is already proposed, as well.

The first will not help with large tag counts that usually require hand-sorting. Examples would be any of the general "version number" tags that lack what they are a version of (such as [2.0] and [2007]). And until the latter is implemented (or any similar system for reducing this impact), the only method to tackle humongous hand-sorted retag jobs will bump a great many of them to the front page.

So I'm coming close to finishing my survey of the ambiguous [language] tag. I haven't taken any action, and instead I've keeping a notepad that groups together posts that would have the same retag associated with it (like [language] -> [rtl] or [language] -> [language-design]). It is also divided between indisputable retags (no question that the retag is appropriate) and disputable retags (I'm unsure if it is technically proper). Once I finish this listing, I'm not sure what to do, though. I bring up [language] but I'm asking that in general, for extremely large hand-sorted retagging jobs:

1. Should I post the listing on Meta for review before taking any action? Should the listing only include posts that require further thought on retagging, or should the indisputable retags also be included?
2. Should I pursue the retagging as an individual, or rally help from other retaggers to handle it?
3. Should I increase the number of retags I do per day for this? Normally I only do around 6-36 retags during low-activity hours. Since the job is particularly large, should I continue at the high end of this rate and spend about 2 months, or would it be preferable to the community that the job is completed at a quicker rate (but still over the course of several days or weeks)? I don't mind taking as long as needed.
4. Would it be wise to target all of the smaller classes of tags first, eventually narrowing down the tag to only one possible option, and flag a moderator to merge the last group all into the one destination tag?
5. Instead of taking any action, should I just silently hold onto the notepad and wait until a soft retag system is implemented before doing anything?

The following questions are about how much content should be contained within a single post for this kind of listing, assuming that each separate post covers at least 20 tagged questions

6. Should tag naming disputes be brought up as part of the listing, or in a separate question? An example of a tag naming dispute is what I brought up here.
7. Should retag merging for some of the destination tags (e.g. [scripting-languages], [scripting-language], [script-language]) be brought up as a separate question prior to the listing, or as part of the listing itself?
8. A third class of division I recently recategorized my notepad with is "Is this tag even appropriate/necessary here?", for cases where the target tag already exists or I honestly don't believe any destination tag is necessary for that question and the tag should just be removed. Should these be part of the listing or brought up in a separate question?

Answer 1

Should I post the listing on Meta for review before taking any action?

This is a good idea, especially in situations where there is some amount of subjectivity involved. The advantage of more eyes on the problem is usually outweighed by the differences of opinion generated by the discussion (it's good to get these opinions out in the open so we can reach consensus on what to do).

Should the listing only include posts that require further thought on retagging, or should the indisputable retags also be included?

Include all of them. It will give the readers and retaggers a solid reference to go by, particularly for those who want to help.

Should I pursue the retagging as an individual, or rally help from other retaggers to handle it?

The advantage of posting a request is to allow others to (a) help you, and (b) come back later on and clean up the little bits that accumulate over time. You also get rewarded with some rep for your contribution to the community. (Note: [retag-request] doesn't necessarily mean you're seeking help from a moderator!)

Should I increase the number of retags I do per day for this? Normally I only do around 6-36 retags during low-activity hours. Since the job is particularly large, should I continue at the high end of this rate and spend about 2 months, or would it be preferable to the community that the job is completed at a quicker rate (but still over the course of several days or weeks)? I don't mind taking as long as needed.

Yes, you can easily do many more than 36 in a day, depending of course on how you spread them out the edits time-wise. Specific to Stack Overflow, even during a period of low activity, the site still moves pretty quick, so you can get through 40-50/hour, and more during periods of high activity (if the retag is simple).

As mentioned, there are soft problems due to retagging, and we have to balance between site maintenance and site usability.

I would err or the side of slow-and-steady in the case of a big manual-only retag, but what I wrote above still applies.

Would it be wise to target all of the smaller classes of tags first, eventually narrowing down the tag to only one possible option, and flag a moderator to merge the last group all into the one destination tag?

This is a good strategy if the questions are in decent shape. However, in a really popular tag, there is a difference in time between when you're done cleaning and when a mod can be flagged down to do the final merge (unfortunately, sometimes this never happens) -- this is bad because new questions could end up categorized incorrectly.

There's also the issue of estimating which tag will be the last one you end up with... that could take a decent amount of time to go through the existing questions to figure it out, and at that point, the time would have been better spent retagging a real sample of the questions so you can get a feel for what the content is actually like (sometimes it's not what you expected at all).

Instead of taking any action, should I just silently hold onto the notepad and wait until a soft retag system is implemented before doing anything?

No, you can proceed whenever you see fit. Just follow the guidelines for flood control, and check the homepage periodically while you're retagging to make sure there isn't a flood issue. Site activity is an organic thing, after all, so if it's quiet for a few minutes (and this does happen sometimes), it's good to slow down and wait for the activity to pick up again.

UPDATE FOR ADDITIONAL QUESTIONS:

Should tag naming disputes be brought up as part of the listing, or in a separate question?

Should retag merging for some of the destination tags (e.g. [scripting-languages], [scripting-language], [script-language]) be brought up as a separate question prior to the listing, or as part of the listing itself?

A third class of division I recently recategorized my notepad with is "Is this tag even appropriate/necessary here?", for cases where the target tag already exists or I honestly don't believe any destination tag is necessary for that question and the tag should just be removed. Should these be part of the listing or brought up in a separate question?

I think you're overthinking this. Keep it simple. Use the same question, so all the discussion and action are kept in one spot. That way it's easy to reference it later on if necessary. Just use [discussion] on the question instead of [support].