I'm sorry. I don't have much time lately, and the reason I'm active one other ones and this one is unfortunately that this one is trickier and thus requires more time commitment than more trivial issues.
To try and get it moving again even with limited time, I'll drop some alternative code I wrote a while back. I wanted to post it integrated and with proper rationale, but well, you're still waiting. So just dropping it is probably better than nothing.

https://gist.github.com/b4n/0f715c19239f501200cfeaefa5a6979c

• IMO (at time of writing I thought it was, at least) easier to understand
• Probably more resources-greedy (likely more memory, likely more CPU), but I don't think it matters at this level
• Fixes quite a few bugs in shortening. I unfortunately forgot what they all were and would need to find them all again, but IIRC the implementation proposed in the PR can count and/or remove sequences not entirely composed of full directories (meaning it could remove half a directory, or nothing at all when it should, with specially crafted path lists sharing longer substrings outside of directory portions or alike). You probably can try the same kind of things I did using a similar sample program as the one in my proposed implementation.

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