Interesting approach. And I am seeing the same "bug" as you are.

I had a quick look at the docs <> but 
couldn't find any mention of special handling of ~, or why it doesn't work 
with that absolute path..

I did notice that if you configure it with

git config core.worktree ~

.. it is expanded to the full /Users/tfnico path inside .git/config.

I also noticed that if I append a dot to the work-tree path when it's full, 
it works:

git --work-tree=/Users/tfnico. ls-files 

By the way, not sure why you first initialize the repo as bare, and then 
manually re-edit it to be non-bare.. Are you following some recipe we 
should know about?

I'm on git version You can see what version of git you have in use 
by running git --version

In any case, I have my doubts on this is actually being bug, and not by 
design. I just can't find the docs right now to explain it.

If you still want to report it as a bug, the place to go is the git 
developer mailing list:

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