I can't see the advantage to having two files open and Open in the same directory. Why would you want that?
(My preference is to leave the root partition case-insensitive, since some apps require that, but to keep all my data and source code on a case-sensitive partition.)
I'm not going to switch my laptop to be case sensitive but I did just run into that issue.
$ touch Open
$ ls open*
ls: open*: No such file or directory
$ ls open
openEdit: Makefile existed in the tarball after makefile, so it would overwrite the real makefile with whatever junk was in Makefile, and it would fail to build.