I think he's referring to system updates, not just installed software.

My usual workflow for setting up a Windows machine goes like this:

  1. Install Windows
  2. Download updates
  3. Reboot
  4. Download updates
  5. Reboot
  ...
  28. Download updates
  29. Reboot
  30. Download updates
  31. Reboot
  32. Install software

It's not great. OS X has been doing cumulative updates from 10.x.0 to 10.x.current for what, a decade now?

MS is rebuilding a lot of essential utilities in their "modern" app framework (including the start menu), but as far as I know, the lower level system updates still get distributed the same way as before, and frequently have long chains of prerequisites.