It wasn't really the processor architecture. Segmented addressing was actually fairly easy if the processor was used only in the way that protected mode was envisioned as working. As the headlined article observes, a lot of this stuff simply wasn't necessary in OS/2 1.x, even though that too had DLLs, callback window procedures, and the multiple tiny/small/medium/large/compact/huge memory models.

The differences were (a) that DOS+Windows was designed so that the same programs could run in both real mode, with overlaying, and 286 protected mode, with segmented virtual memory; and (b) that to really save on RAM DOS+Windows had ideas such as the data segments for DLLs being globally shared across all processes. These added all of the complications mentioned in the headlined article and more besides. It was the operating system, not the processor architecture.