I'm definitely thinking it has to be a file system thing. I'd also tried to get it to run under Wine in Linux - in theory it works, but in practice it didn't.
I might plug in one of my spare flash drives and try installing there, since those aren't using NTFS at all.
Active Sims: rFactor, GTR2
Inactive Sims: NR 2003, RACE '07, F1C, GPL, GP3, GP2
citizen059 on Steam
citizen059 on Planetside 2 (Waterson - Vanu Sovereignty)