Replace "play poker with his buddies" with "watch movies his buddies are talking about" and "Joe's Terrible Malware-Infested Poker Site" with "Netflix's DRM-Infested Site" and the results are the same every time. Your grandpa isn't likely to care if Netflix has DRM or not so long as it doesn't stop him watching movies. If Netflix, because it's the brand he and his buddies trust, tells him to install a thing to keep watching movies, he installs the thing.
Maybe, maybe you might be able to convince your grandpa to stop watching videos using that thing he installed because it's bad for his computer's health... but there are a lot of "grandpas" out there, it's a huge category of people that "I just want to do the thing and I don't care how so long as it works and is convenient".
I don't think this a question of timeframe, it's a question of do the right thing for the most users. There are a lot more "grandpas" than there are DRM-fighting or at least DRM-wary concerned citizens like you or me.
This is clearly written from the perspective of somebody who never did help desk work or helped family or friends with computer problems.
It's the same logic that leads to them to support JavaScript.