Moving from indexed & folder-based to imported & tag-based

Hello, all.
I’m creating this post to ask for advice regarding a transition I’m about to make.

I have a DEVONthink database for keeping content saved from the web - bookmarks and PDFs - across a wide range of topics.
These are organised using folders/groups, which can go up to 4 levels deep.
All the content is indexed, rather than imported.

I want to transition to a pure tag-based approach, so that whenever I add an item, instead of having to think and specify a group where it should go, I will just specify the database and the appropriate tags.
Because of this, I think it also makes sense for the content to be imported into the database rather than indexed.

I have already created a separate database with which I’ve been experimenting this approach.
Now I would like to migrate the content in my indexed folder-based database. It contains approximately 2000 files and 424 groups.
I would like the folder structure to be converted to a tag structure (ordinary tags). For example, if I have the following 4 folders:

 |- Apple
      |- iOS
          |- Documentation

then I would like any items in the Documentation group to have the tags Documentation, iOS, Apple and Technology.
I am familiar with the Group Tags concept, but I would like to use ordinary tags instead.

  1. Should I
    A) do these changes within the same database where this content is, or
    B) keep that database as it is and copy the content to the database with which I’m already experimenting with the “tag-based & imported content” method?
  2. Depending on the answer above, what steps would you advise me to follow?
  3. Is it possible to automate the process of tag creation and tagging as I described above, or would I have to manually create the tags and tag the items myself?

Thanks in advance!

I would like the folder structure to be converted to a tag structure (ordinary tags).

The documents are not going to only reside in the tags group of a database.

What’s the issue with using group tags?

Method B requires no less time than method A; in fact perhaps more effort in method B. Tags are just another form of grouping documents. It’s worth stepping back and thinking about whatever it is about the current approach that bothers you, before creating a new approach that might have the same pain point.

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Personally I feel that group tags do not allow me to completely stop thinking about groups/folders.
Some tags would be under Tags while others would be represented as Group Tags.

I also found out that with group tags, when an item gets assigned a 2nd tag, the concept of replicants comes into the picture. My items turn red and italic when this happens because I have the option “Mark duplicates and replicants in color” enabled in the Settings. (And I want it enabled.)

This does not happen with ordinary tags, and I prefer it that way.
(I understood from this comment of yours that for many years the term “replicant” has been used as well when an item is tagged with an ordinary tag.
But the app clearly treats both situations differently, and I find that it makes sense not equating “assigning ordinary tags” with “creating more replicants”)

Still, one way to go about this could involve using group tags during a transition phase. It would be like this:

  1. Keep the existing folder structure and enable group tags.
  2. Over time, manually tag the items with ordinary tags and delete their group tag.

Does this sound feasible?
Are there other alternative methods?

Thank you for your advice.

My view on this is: perhaps it requires a bit more thinking when saving items, but in my opinion it is much better later when it comes to finding content, by reducing the need to remember where items were stored, and using the tags filter instead.

OK, Remember that DEVONthink search is so excellent that it is never important to remember where anything is – group or database or wherever. It’s also as easy to forget which tag is assigned as it is to forget which group. Tags/groups – they’re both the same concept.