Alexandre Julliard:
Win16 applications don't need vm86, and work just fine on 64-bit.
OK, that means that with some LDT tricks Win16 apps may work in Wine. I'm not 100% sure but I know the LDT offset trick works for DPMI applications in DOSEMU which I tested a bit last year. Wine can also execute some DOS apps, and those won't be possible in i386 without zero mapping unless Wine acquires a CPU emulator or someone can think of another solution.