Windows 64-bit versions dropped support for 16-bit programs and all 32-bit drivers. Microsoft did the same thing as Apple (which partly led to the Vista debacle), so even they recognized that there is a limit to legacy support.
Arguably OS X's transition to 64-bit was smoother since they allowed 32-bit drivers to run on the first 64-bit versions, while Microsoft just dropped support altogether and forced OEMs to write 64-bit drivers for everything they wanted certified to run on Windows 7.
That's a totally ways off comparison - When 64-bit Windows dropped 16 bit support, Microsoft was still selling 32-bit Windows. Most importantly very few were still running 16-bit code at the time - even when compared to how many people still run 2007 Mac Pros.
Microsoft making vendors write 64-bit drivers was a good thing - didn't hurt me as a consumer. Microsoft's 64-bit transition was arguably the best - people buying Windows 7 machines today don't even notice it for the most part.
But that's completely besides the point - 64bit is behind us. We are talking supporting older 64-bit capable hardware here.