Good stuff man.

"To which the answer is: You're not."

I think that's what's changed and people just haven't picked up on. 15 years ago, a knowledgeable user had 3-10 major websites, and 1-5 real life services (Cable, utilities), and maybe a few game accounts. There was one browser, and you got a new computer... never.
Worst case scenario, if something was compromised, you'd be aware, and it was isolated.
Nowadays there are so many aspects to online presence. Minumum password requirements, site ownership changes, log-ins just to log-in. Different browsers, phones authentication, apps that log you out of websites.

To have "my password" is such a crazy perception and expectation.