Except this person has a very straightforward workaround: Use the X button. Win95 could have removed the system menu when they replaced it with an icon of the application, but so many programs were fiddling with the frame drawing that some probably couldn't be closed without the system menu.
> "Up and down" made sense. "Line and box"? Windows 95 brought a lot of advantages, but we lost so much of the little touches along the way.
This is a typical migration problem: The line and box icons represent the Taskbar and the full screen window, so they actually make much more sense than Up and Down arrows, but this user still hasn't adapted. Hard to blame him: With Aero, windows don't look like rectangles anymore and bubbles would better represent the Taskbar than a line.
For the same historical reason he likes double clicking for powerful actions, except click vs double-click doesn't have any logic or consistency anymore, mostly since we introduced the Web and the single click. <s>No click is even enough to upgrade to Windows 10 </s>.
Heck, my parents keep double-clicking everywhere in Windows, including in web pages. Submitting forms twice is so much a problem in companies that jQuery plugins exist to discard the second click on links and buttons.
Consistency and user migration path are hard problems. It's necessary to remove features sometimes.