So basically, it's Just Not Possible to write something that's the Macintosh equivalent to WINE (a compatibility library), because Apple made the System Software reliant on hardware-specific behavior. The only way to run Mac executables is to run the Mac OS on (real/emulated) hardware.

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It's actually been done already. Look up "Ardi Executor".

http://en.wikipedia.org/wiki/Executor_(software)

It never worked that well (allegedly) for the same reason the Wine has problems, but there it is. According to the wiki page the source code for it has been released so if you want to hack, have at it. The released Executer binaries ran on x86 so they were of course intimately linked to the syn68k CPU emulator, but in principle there's probably no reason why you couldn't substitute native execution on NetBSD m68k or the like... although since Mac software assumes it's running in privileged mode with no memory manager trapping illegal instructions might be a bear.