Most translation tools are really hard to use when you try to handle a long text, so the translators have to use a HTML editor anyway. Use separate files, but use the language prefix as directory name:
- en
- main.html
- help-main-options.html
- help-special-options.html
- de
- main.html
- help-main-options.html
- help-special-options.html
That’s easier to handle for translators and for you too.
You could also set up a WordPress site for translations and use a custom post type, so translators can use the regular editor (outdated example), and you handle just the import and export.
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