WRT your first point, well, he's an eat-your-own-dogfood philosopher, and he sets an example to what is possible with his own behaviour. And he just does not make trade-offs in his views. What we should collect from them is what's useful to us. It would be kind of hypocritical if he was telling non-free software is evil, but recommended some such software.

WRT your second point, that is subjective and ad hominem. I live in Emacs and without GNU I was stuck with Windows. Without GNU none of the good things we have today would've existed, Linux wouldn't have existed, we were all programming in ASP.NET or C# or what not. So even if he is an asshole, he's a very, very, very important one.