I mean, I can't speak for any other long-time Mac users, but...

> I regularly have to deal with 50+ character naming conventions where the first 38 characters are the same among many files.

...that's arguably a kind of unusual situation.

I don't think you're necessarily wrong, to be fair! It's just that in over two decades of owning Macs and at least a decade before that of using them off-and-on, I've never been in a situation where I thought, "man, the text field for entering a file name is just way too short."

The thing is, 38 chars is arbitrary limit from bygone era when screen space was precious and UI had to make sure dialog boxes fit no matter what. It's not like Apple can do hidpi UI but can't overcome 38 character limit for file name entry widget. It'd be small qol fix but no, for some reason other commenters need to defend it and point out that OP should just organize their files better. I don't understand, truly I don't.

If your workflow is dependant on many files, and with that naming convention because of it - there’s a good chance the workflow could be cleaned / simplified greatly. Wether it’s worth the effort or not, I don’t know - but lots of tools / freedoms / restrictions make certain processes possible and it’s always worth revisiting.

The naming conventions that require >38 characters come from a vast number of business entities that I have worked with through the years: Customer_Project_Subtask_Blaa How does anyone in the real working world not have this issue?

There's already a sibling comment that suggests this, but to elaborate, this is how I would typically organize something like that:

    /home/my_user/
      Customer/
        Project/
          Subtask/
            Foo.txt
            Bar.txt

Is there a reason why you can't just use nested folders?

...folders?