While trying to dodge issues with case-sensitivity, I stumbled on a somewhat
effective solution: the old Mac OS Hierarchical File System (HFS). HFS is case
insensitive and supports symlinks, making it very useful for Wine. The drawbacks
are that it's slow compared to modern file systems, the max file size is 2GB
and filenames are limited to 31 bytes. It will likely have problems running
programs that frequently access the HDD and obviously won't run anything
with a file larger than 2GB, but many older programs seem to work well. In
particular, I found it useful for running games that I use a lot of mods with
which don't necessarily use the same capitalization, such as Morrowind and
Oblivion. HFS only has limited support in most distros by default, largely
remaining as legacy support, but tools like hfsprogs add more functionality.
CIOPFS is probably a much better option for those that know how to use it, but
the lack of documentation for it put me off. Anyway, I hope somebody finds this
information to be helpful.