Lol, I'm a software developer that started by writing legacy windows software, I know exactly how much (little) has changed.
It is this perspective that exposes your bias and colors your perception.
We live in a post-Heartbleed world. We live in a post-UAC world. We constantly find new bugs and vulnerabilities, and they cannot always be patched without massive changes to the architecture. We cannot forever maintain old systems that cultivated bad habits in it's users.
Not all change is good, but all change is inevitable.