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That's a really cool project! Definitely going to look into it for some of our more complicated courses, but for this course compilation is usually under a half-second so it's not the compilation that's slow (it's the way we are tearing down an entire VM after every submission, we are working on changing that now)
Ah. Maybe consider a FreeBSD jail with a union mounted filesystem if you can get away with using a non-Apple (GNUstep/GCC?) toolchain. The teardown on a jail is as fast as the chroot syscall. ;-) Or even better, use ZFS snapshots as your sandbox. Copy on write kicks butt. See: http://vocalbit.com/article/402/freebsd-jails-using-zfs-and-...
GNUstep/GCC is possible, but you lose support for all of the above, blocks, and several other recent additions to the Objective-C language.