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From: Adam Porter <adam@alphapapa.net>
Subject: Re: CUSTOM_ID vs ID
Date: Fri, 09 Aug 2019 06:13:57 -0500
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Nathan Neff <nathan.neff@gmail.com> writes:

> I have a lot of org files and one of the main purposes of links is to be able to link
> to different headings across documents.  This seems to imply I should use 
> the ID property.
>
> However, I usually *do* manually assign IDs (not CUSTOM_IDs) myself.   The
> reason is so I can reasonably search for the ID within my org files and that the link
> ID makes some sense to me.
>
> For example, if I see a link to "id:keyboard_shortcuts" I can tell where it's going.
> Later on, if I want to insert a link to my keyboard shortcuts heading in another place
> in my org files,  I can make a guess of the ID I want to link to.
>
> So, I guess I'm okay manually assigning ID properties, as long as I
> don't have conflicts.

FYI, you may find the package org-bookmark-heading useful.