Earlier quoted context omitted.
You're assuming all paths are created and consumed by humans. Automated processes could easily generate and work with long paths for perfectly-valid reasons. A limit this low causes grief for people that "deserve" better.
Indeed, I've even managed to run into this issue on linux, where an openembedded build would fail because the list of files passed to a command in a shell script would not fit in the buffer of arguments (about 5K IIRC). Fixing it would require recompiling the kernel.
Yes its freaking annoying, but I think having a path > 260 chars or a need to pass 5000+ bytes in as line arguments all count as "code smells".
If you are hitting these issues, something else is wrong and in my experience, fixing the other things is much much more productive.