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.
