As long as we're playing "what if," it's worth reflecting on all the hair-raising hacks and tricks Microsoft had to play to deal with the x86's quirks as they built Windows. XMS/EMS and DPMI were also incredibly painful engineering feats.
While the M68K had its own growing pains (as seen with the evolution of the Macintosh), none of them seemed nearly as onerous as what was done to squeeze a few more years out of MS-DOS compatibility.