Wil Shipley and his Red Box
Wil Shipley thinks that WINE was the next big thing. Don't agree. I can see how WINE could be used by game porting companies after the x86 move (no native GUI to screw up there), but if Apple shipped WINE with OS X, the risk would be too big that Mac versions of software wouldn't get developed, and the Mac UI would die.
As Soeren alludes, this already happened to OS/2, which got few native apps because its Windows compatibility was too good.
And forget the rumored Red Box it's a warmed-over rumor that didn't come true in the Rhapsody days. And it's also unlikely that the Red Box would have the Aqua UI. Apple could have done that for Classic and they didn't. They won't do it for Windows. Not to mention that would mean mapping various aspects of the Windows GUI to Mac equivalents, at which enough people have failed already.
Porting to Macs will be a lot easier with the main hardware differences gone. Making it any easier doesn't provide enough benefit for the effort involved.