NTFS absolutely supports case sensitivity but, presumably for consistency with FAT and FAT32 (Windows is all about backwards compatibility), and for the sake of Average-Joe-User who’s only interaction with the filesystem is opening Word and Excel docs, it doesn’t by default.
All that said, it can be set on a per-directory basis: https://learn.microsoft.com/en-us/windows/wsl/case-sensitivity
Yeah, everything that’s already been said, except that I specifically chose an off-the-shelf Synology NAS with Docker support to run my core setup for this exact reason. It needs a reboot maybe once or twice a year for critical updates but is otherwise rock solid.
I have since added a small N100 box for things that need a little extra grunt (Plex mainly) but I run Ubuntu Server LTS with Docker on that and do maintenance on it about as often as I reboot the NAS.