I think you're missing luigi's point. He's simply remarking that the OP didn't have to advocate a change in use pattern in order to lend his expertise to his friend's father. Instead, the OP made the choice not to use his time assisting someone who doesn't want to "go all Apple". Of course, the OP isn't obligated to offer free tech support, but he certainly could have helped.
Constructive help would've probably helped the user make an informed decision to 'switch'. OP probably means that going a step beyond and even advocating a patch work strategy might have better convinced the user to switch(in time...) rather than advocacy.
Why don't you explain why his help would have "set the guy back?". The closest the article comes to justifying this claim is that (from memory) "[the author] doesn't know shit about outlook or windows architecture". But as luigi and vectorpush have noted, as someone with general tech savvy, he could still have helped.
You can 1) throw in a suggestion, 2) blindly suggest whatever works for you as the best way, 3) learn about the goals, setup, and knowledge of the user as the first step. The point of the article is: 2) is a mistake.
