Good to know!
So, I modernized the inner workings a bit, and now I'm running an Apache2.4 server on Windows 7 Professional x64. It's not as simple, but it's more maintainable and has fewer limitations (some of the filenames were mangled after being converted to DOS 8.3). I'm toying with setting it up on an Ubuntu VM as well (maintainable and portable, all at the same time!), but this works for now.
It's presently on its own 250 GB hard drive, so I think I'll put it in another computer at some point, as it's currently residing in my "summer daily driver" (the somewhat expendable computer I'm using during fire season, with my nice, difficult to replace Mac Pro safely in the car so I don't have to drag it out of the house every time there's an evacuation). This is why the server has been so erratic.
At some point, I'll have to figure out how to set up a mirror so there aren't disruptions.
c