That fellow takes a long time to say very little, but of course he’s basically right — you can run Win7, or Vista, or XP, or 2K, or 98, or 95 forever, but what you can do with them decreases as time goes on, and their security suffers more and more.
Win7’s desktop interface (GUI) is still my favorite. But I no longer allow my Win7 hosts to connect the Internet. Why should they? There are no security or application updates out there for Win7. But I have a few old Windows-only programs that I still need to run, and either I prefer to run them on Win7, or in a couple cases they won’t run on Win10.
My Win7 systems are “air-gapped”, meaning they have no connection to any of my other computers. When necessary I exchange files using a USB Flash drive which gets malware-scanned daily. So it’s possible to keep using Win7 with some degree of safety, with strict limits on what it does.
But after Jan 2020 I will never again use Win7 as my platform for websurfing or any other internet-connected application.
I was working on a cybersecurity incident with a customer. They're not PubSec, but their data is valuable. About half of their datacenter was airgapped, and they said the same, "we only use known-safe media, scan it daily, etc." Somehow a nasty bit of code was rampaging through their supposedly safe network, deleting random files, corrupting backups, the works!
Turns out their primary scanning utility doesn't do much more than a simple heuristics check against data being put on these trusted thumb drives, and someone neglected follow "clean source" principles, downloading what they thought was a driver for new hardware that turned out to be malicious code. Had they checksummed the driver data (there wasn't one), they would've known better.
Moral of the story: don't trust "scanners." Their heuristics scanner couldn't tell that the "driver" was really malicious code.
Most malicious data these days don't trip "malware" or "antivirus" scanners. Malware and antivirus are 20+ year old infection vectors. People still have a false sense of security from scanners like Norton, McAfee, AVG. They're functionally useless nowadays, and most of them are bloatware or worse.
Who the heck would bother hacking a Win 98 machine, in 2020?
Granted that such is almost useless on the web in 2020.
But, yeah, I actually do have a Win 98 machine still running a couple old apps that won’t run easily on Win 7, and all transfers from that machine are by scanned flash drive.