> At what point in history have you owned a particular piece of hardware [...] and installed a major OEM operating system release a full 7 years after release without issue?

A few years ago, I installed Windows 10 on a cheap laptop from 2004—the laptop was running Windows XP, had 1GB of memory, a 32-bit-only processor, and a 150GB hard drive. The computer didn't support USB boot, but once I got the installer running, it never complained that the hardware was unsupported.

To be fair, the computer ran horrendously slow, but nothing ever crashed on me, and I actually think that it ran a little bit faster with Windows 10 than with Windows XP. And I used this as my daily driver for about 4 months, so this wasn't just based off of a brief impression.